SUBSTITUTED α-DIALKYLAMINOALKYL-1-NAPHTHALENE-METHANOLS. IX. α-(2-DIALKYLAMINOETHYL)-α-METHYL ARYLMETHANOLS<sup>1</sup>

Spaeth, Earl C.; Geissman, T. A.; Jacobs, Thomas L.

doi:10.1021/jo01174a017

Cited by 10 publications

(5 citation statements)

References 11 publications

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“…It had the m.p. 223-224°, compared with the value 210°r eported by Friedlánder and Weisberg (13), and was identical with the acid obtained by the action of carbon dioxide on 4-chloro-l-naphthylmagnesium iodide (14).…”

supporting

confidence: 84%

SUBSTITUTED α-DIALKYLAMINOALKYL-1-NAPHTHALENEMETHANOLS. II. 1-HALONAPHTHALENES IN THE FRIEDEL AND CRAFTS REACTION¹

Tl¹,

Winstein²

1946

J. Org. Chem.

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4-Haloacetonaphthones were needed as starting materials for the synthesis of certain amino alcohols (1). It appeared probable that these could be synthesized most readily by the Friedel and Crafts reaction on halonaphthalenes, and this has proved to be the case. Schweitzer (2) first prepared a bromoacetonaphthone by the reaction of 1-bromonaphthalene, acetyl chloride, and aluminum chloride in carbon disulfide but did not prove the structure of the product. Dziewonski and Stembach (3) carried out the same reaction and showed that 4-bromo-1 -acetonaphthone was the principal product, by oxidation to 4-bromo-1 -naphthoic acid. Other examples of the Friedel and Crafts reaction with 1 -halonaphthalenes have been reported by Mayer and Muller (4) and by Fieser and Desreux (5). The latter found that the reaction between 1 -chloronaphthalene and 4-methylhydrindene-7carboxylic acid chloride failed when excess 1 -chloronaphthalene was used as the solvent, but in tetrachloroethane an 82% yield of a substituted benzanthrone was obtained. No account was taken of isomers present in minor amounts in

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supporting

confidence: 84%

SUBSTITUTED α-DIALKYLAMINOALKYL-1-NAPHTHALENEMETHANOLS. II. 1-HALONAPHTHALENES IN THE FRIEDEL AND CRAFTS REACTION¹

Tl¹,

Winstein²

1946

J. Org. Chem.

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“…4,4'-Dimethoxy-l,l'-binaphthyl (II) was formed by the coupling of 4-iodo-lmethoxynaphthalene or from 4-bromo-1 -methoxynaphthalene. 7 The product proved to be identical with that obtained by the methylation2•8 of I…”

Section: Discussionmentioning

confidence: 57%

Macro Rings. VII. The Spectral Consequences of Bringing Two Benzene Rings Face to Face¹

Cram¹,

Allinger²,

Steinberg³

1954

J. Am. Chem. Soc.

204

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“…237-239°( uncorr.). No depression was observed on admixture with material prepared in this laboratory (16) by carbonation of the Grignard reagent from 4-methoxy-l-bromonaphthalene.…”

mentioning

confidence: 73%

SUBSTITUTED α-DIALKYLAMINOALKYL-1-NAPHTHALENE-METHANOLS. VI. SOME MANNICH KETONES AND DERIVED PROPANOLAMINES¹

Winstein¹,

Tl²

1946

J. Org. Chem.

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In the search for antimalarial drugs, the group at the National Institute of Health has investigated as well as ethanolamines, the amino alcohols of type III with the propanolamine side chain. At the suggestion of Dr. Lyndon F. Small, we undertook the preparation of the propanolamines in which the naphthalene nucleus was substituted with a methoxyl group or a halogen atom just as we did in the case of the ethanolamines (1). COCHs COCH2CH2NR2 CH(OH)CH2CH2NR2The most direct approach to compounds of the type III is, of course, through the Mannich ketones II. This is the method used at the National Institute of Health, and the one we used for the preparation of several propanolamines. Our preparations in this connection and some observations on the Mannich reaction are reported in this paper. In certain cases, sometimes for interesting reasons, the preparation by way of the Mannich ketones proved impossible, and a number of propanolamines were prepared by other methods discussed in the following article (2).In the course of our work we prepared Mannich ketones II from 4-methoxyand 4-chloro-l-acetonaphthone and several dialkylamines (Table I). In these preparations nitromethane possessed advantages over several more conventional(3) solvents and is recommended for trial in other cases.In attempting to prepare an amino ketone from 4-methoxy-l-isobutyronaphthone IV in order to arrive eventually at a branched chain amino alcohol V,

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SUBSTITUTED α-DIALKYLAMINOALKYL-1-NAPHTHALENE-METHANOLS. IX. α-(2-DIALKYLAMINOETHYL)-α-METHYL ARYLMETHANOLS¹

Abstract: Because of the availability of l-dialkylamino-3-butanones through the Mannich synthesis, compounds of the type aryl-C (CH3) (OH) CH2CH2NR2 should readily be prepared by a Grignard reaction as shown in the following equations:

Cited by 10 publications

References 11 publications

SUBSTITUTED α-DIALKYLAMINOALKYL-1-NAPHTHALENEMETHANOLS. II. 1-HALONAPHTHALENES IN THE FRIEDEL AND CRAFTS REACTION¹

SUBSTITUTED α-DIALKYLAMINOALKYL-1-NAPHTHALENEMETHANOLS. II. 1-HALONAPHTHALENES IN THE FRIEDEL AND CRAFTS REACTION¹

Macro Rings. VII. The Spectral Consequences of Bringing Two Benzene Rings Face to Face¹

SUBSTITUTED α-DIALKYLAMINOALKYL-1-NAPHTHALENE-METHANOLS. VI. SOME MANNICH KETONES AND DERIVED PROPANOLAMINES¹

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SUBSTITUTED α-DIALKYLAMINOALKYL-1-NAPHTHALENE-METHANOLS. IX. α-(2-DIALKYLAMINOETHYL)-α-METHYL ARYLMETHANOLS1

Abstract: Because of the availability of l-dialkylamino-3-butanones through the Mannich synthesis, compounds of the type aryl-C (CH3) (OH) CH2CH2NR2 should readily be prepared by a Grignard reaction as shown in the following equations:

Cited by 10 publications

References 11 publications

SUBSTITUTED α-DIALKYLAMINOALKYL-1-NAPHTHALENEMETHANOLS. II. 1-HALONAPHTHALENES IN THE FRIEDEL AND CRAFTS REACTION1

SUBSTITUTED α-DIALKYLAMINOALKYL-1-NAPHTHALENEMETHANOLS. II. 1-HALONAPHTHALENES IN THE FRIEDEL AND CRAFTS REACTION1

Macro Rings. VII. The Spectral Consequences of Bringing Two Benzene Rings Face to Face1

SUBSTITUTED α-DIALKYLAMINOALKYL-1-NAPHTHALENE-METHANOLS. VI. SOME MANNICH KETONES AND DERIVED PROPANOLAMINES1

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SUBSTITUTED α-DIALKYLAMINOALKYL-1-NAPHTHALENE-METHANOLS. IX. α-(2-DIALKYLAMINOETHYL)-α-METHYL ARYLMETHANOLS¹

SUBSTITUTED α-DIALKYLAMINOALKYL-1-NAPHTHALENEMETHANOLS. II. 1-HALONAPHTHALENES IN THE FRIEDEL AND CRAFTS REACTION¹

SUBSTITUTED α-DIALKYLAMINOALKYL-1-NAPHTHALENEMETHANOLS. II. 1-HALONAPHTHALENES IN THE FRIEDEL AND CRAFTS REACTION¹

Macro Rings. VII. The Spectral Consequences of Bringing Two Benzene Rings Face to Face¹

SUBSTITUTED α-DIALKYLAMINOALKYL-1-NAPHTHALENE-METHANOLS. VI. SOME MANNICH KETONES AND DERIVED PROPANOLAMINES¹