Nitration of antibiotic X-537A and facile conversion to 6-hydroxy-2,7-dimethyl-5-nitroquinoline

Westley, JW; Schneider, Judith C.; Rh, Evans; Williams, Tracie L.; Ad, Batcho; Stempel, Arthur

doi:10.1021/jo00822a036

Cited by 10 publications

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“…Examples of halogenation [4], nitration [S], and azocoupling [6] leading to monosubstituted products have been published. Under more severe conditions of bromination and nitration, dibromo and dinitro derivatives are obtained in which the second electrophile has displaced the carboxyl group [4] [ 5 ] .…”

Section: Discussionmentioning

confidence: 99%

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ChemInform Abstract: CHEMICAL DEGRADATION OF LASALOCID. (A). THE MANNICH REACTION. (B) BAEYER‐VILLIGER OXIDATION OF THE RETRO‐ALDOL KETONE

Coffen

Katonak

1981

Chemischer Informationsdienst

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Section: Discussionmentioning

confidence: 99%

“…A sample from a different preparation was purified by preparative TLC. Lasulocid aldehyde (5). a) A solution of crude anil 4 (3.1 g) in THF (50 ml) and 3N HCI (10 ml) was stirred overnight at RT.…”

Section: -mentioning

confidence: 99%

ChemInform Abstract: CHEMICAL DEGRADATION OF LASALOCID. (A). THE MANNICH REACTION. (B) BAEYER‐VILLIGER OXIDATION OF THE RETRO‐ALDOL KETONE

Coffen

Katonak

1981

Chemischer Informationsdienst

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“…The oil was chromatographed on 100 g of silica gel using a linear gradient from 1 1. of 1:4 methylene chloride-hexane to 11. of methylene chloride. The first fraction was concentrated and crystallized to give 81 mg (14%) of 5: mp 45-47°; nmr (CD-Cls) 1.94 (s, 3, CH3C=), 2.20 (s,3,aromatic CH3),2.20,2.84 (m, 4, /vie = 8 Hz, CH2CH2), 6.47 (s, 1, CII=C), 6.59, 6.82 (AB, 2, /ortho = 9 Hz, aromatic); mass spectrum m/e 174 (M+).…”

Section: Experimental Section7mentioning

confidence: 99%

Pyrolytic cleavage of antibiotic X-537A and related reactions

Westley¹,

Evans²,

Williams³

et al. 1973

J. Org. Chem.

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Notestions will be those derived from V which we have found to brominate at a rate comparable with that of I.The kinetic results support the failure of Swain and Dunlap1 to detect appreciable deuterium incorporation in unreacted III under conditions where it had undergone 57% conversion to V in alkaline D20. Experimental SectionMaterials.-3-Bromo-2-butanone [n80D 1.4575, bp 85°(118 mm)] and l-bromo-2-butanone [m20d 1.4676, bp 104°( 118 mm)] were prepared by the procedure of Catch, et al.8 Upon hydrolysis of the corresponding bromobutanones (5 g, 0.033 mol) in aqueous sodium hydroxide (100 ml, 2 M) at room temperature there was obtained l-hydroxy-2-butanone (n20d 1.4271, bp 158°) and 3-hydroxy-2-btitanone (n20D 1.4168, bp 144°), respectively, in high yield.Kinetics.-Reactions of the bromobutanones with sodium hydroxide were initiated using a Durrum Gibson stop-flow apparatus fitted with a T-jump cell. The syringes contained bromo ketone (0.005 M) and sodium hydroxide (0.001 M), respectively. Reactions were followed by monitoring change in conductivity between the plates of the T-jump compartment.9 A Radiometer automatic titration assembly was also used for an alternative pH-Stat procedure.Reactions of 1-and 3-bromo-and of 1-and 3-hydroxy-2butanone (0.005 M) with bromine (0.024 M) in aqueous hydroxide (0.1 M) were initiated by stop-flow techniques and followed by colorimetric observation of the change in absorbance at 398 nm.Stop-flow results were consistent with those obtained using a Gilford 2400 spectrometer to monitor (at 350 nm) consumption of BrO~in a solution which initially contained hydroxide (0.01 M), bromine (0.003 M), and bromo ketone (<0.001 M).

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ChemInform Abstract: NITRIERUNG DES ANTIBIOTICUMS X‐537A UND DIE EINFACHE UMWANDLUNG IN 6‐HYDROXY‐2,7‐DIMETHYL‐5‐NITRO‐CHINOLIN

Westley¹,

Schneider²,

Evans³

et al. 1972

Chemischer Informationsdienst

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Nitration of antibiotic X-537A and facile conversion to 6-hydroxy-2,7-dimethyl-5-nitroquinoline

Cited by 10 publications

References 0 publications

ChemInform Abstract: CHEMICAL DEGRADATION OF LASALOCID. (A). THE MANNICH REACTION. (B) BAEYER‐VILLIGER OXIDATION OF THE RETRO‐ALDOL KETONE

ChemInform Abstract: CHEMICAL DEGRADATION OF LASALOCID. (A). THE MANNICH REACTION. (B) BAEYER‐VILLIGER OXIDATION OF THE RETRO‐ALDOL KETONE

Pyrolytic cleavage of antibiotic X-537A and related reactions

ChemInform Abstract: NITRIERUNG DES ANTIBIOTICUMS X‐537A UND DIE EINFACHE UMWANDLUNG IN 6‐HYDROXY‐2,7‐DIMETHYL‐5‐NITRO‐CHINOLIN

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