SUBSTITUTED α-DIALKYLAMINOALKYL-1-NAPHTHALENE-METHANOLS. VIII. 5-, 6-, AND 7-CHLORO DERIVATIVES<sup>1</sup>

Jacobs, Thomas L.; Winstein, S.; Henderson, Robert B.; Bond, John; Ralls, Jack W.; Seymour, D. E.; Florsheim, Warner H.

doi:10.1021/jo01173a004

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1947

2007

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Cited by 7 publications

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“…240-242°. Probably the lower-melting 6-chloro-l-naphthaldehyde (8) was present in the mother liquors.…”

mentioning

confidence: 99%

1,6- (OR 2,5-) DISUBSTITUTED NAPHTHALENES¹

Hurd¹,

Fancher²,

Bonner³

1947

J. Org. Chem.

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The present study concerns itself with various new approaches to the problem of attaching substituents at the 1,6 positions of naphthalene, since several compounds of this type were desired for antimalarial investigations. One such approach was the Gattermann reaction with 2-chloronaphthalene, hydrogen cyanide, and aluminum chloride. An aldehyde was obtained, m.p. 100-102°, which changed to 7-chloro-l-naphthoic acid on oxidation. It was, therefore, the previously undescribed 7-chloro-1 -naphthaldehyde. The fact that the crude aldehyde melted at 82-85°s uggests that 6-chloro-l-naphthaldehyde (m.p. 83-84°) was also present.Several new compounds were made from Cleve's acid, 5-amino-2-naphthalenesulfonic acid. These included sodium 5-cyano-2-naphthalenesulfonate made

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“…240-242°. Probably the lower-melting 6-chloro-l-naphthaldehyde (8) was present in the mother liquors.…”

mentioning

confidence: 99%

1,6- (OR 2,5-) DISUBSTITUTED NAPHTHALENES¹

Hurd¹,

Fancher²,

Bonner³

1947

J. Org. Chem.

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“…235-239°( uncorr.) available from the separation of the mixture of acids from the reaction of chlorobenzene with methyl furoate (5). Further, samples of the supposed a-di-n-butylaminomethyl-2-chloro-1 -naphthalenemethanol hydrochloride, m.p.…”

mentioning

confidence: 99%

Correction of Structure for Several Supposed 2-Substituted 1-Naphthalene Derivatives

Winstein¹,

Jacobs²,

Day³

1948

J. Org. Chem.

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Saul Winstein: Contributions to Physical Organic Chemistry and Bibliography

1972

Progress in Physical Organic Chemistry

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SUBSTITUTED α-DIALKYLAMINOALKYL-1-NAPHTHALENE-METHANOLS. VIII. 5-, 6-, AND 7-CHLORO DERIVATIVES¹

Abstract: Since certain a-dialkylaminomethyl-2 or 4-chloro-l-naphthalenemethanols(1, 2, 3, 4) possessed considerable antimalarial activity, it was desirable to study the effect of further varying the position of the halogen. This paper reports the

Cited by 7 publications

References 6 publications

1,6- (OR 2,5-) DISUBSTITUTED NAPHTHALENES¹

1,6- (OR 2,5-) DISUBSTITUTED NAPHTHALENES¹

Correction of Structure for Several Supposed 2-Substituted 1-Naphthalene Derivatives

Saul Winstein: Contributions to Physical Organic Chemistry and Bibliography

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SUBSTITUTED α-DIALKYLAMINOALKYL-1-NAPHTHALENE-METHANOLS. VIII. 5-, 6-, AND 7-CHLORO DERIVATIVES1

Abstract: Since certain a-dialkylaminomethyl-2 or 4-chloro-l-naphthalenemethanols(1, 2, 3, 4) possessed considerable antimalarial activity, it was desirable to study the effect of further varying the position of the halogen. This paper reports the

Cited by 7 publications

References 6 publications

1,6- (OR 2,5-) DISUBSTITUTED NAPHTHALENES1

1,6- (OR 2,5-) DISUBSTITUTED NAPHTHALENES1

Correction of Structure for Several Supposed 2-Substituted 1-Naphthalene Derivatives

Saul Winstein: Contributions to Physical Organic Chemistry and Bibliography

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Product

Resources

About

SUBSTITUTED α-DIALKYLAMINOALKYL-1-NAPHTHALENE-METHANOLS. VIII. 5-, 6-, AND 7-CHLORO DERIVATIVES¹

1,6- (OR 2,5-) DISUBSTITUTED NAPHTHALENES¹

1,6- (OR 2,5-) DISUBSTITUTED NAPHTHALENES¹