Methyl vinyl ketone → 4-Methyl-5,6-dimethoxy-8-nitroquinoline

HRID 1863112Notes

Reaction equation

HRID 1863112 reaction equation
[CH3:1][O:2][C:3]1[C:9]([O:10][CH3:11])=[CH:8][C:6]([NH2:7])=[C:5]([N+:12]([O-:14])=[O:13])[CH:4]=1.[CH:15]([C:17]([CH3:19])=O)=[CH2:16]>>[CH3:11][O:10][C:9]1[C:3]([O:2][CH3:1])=[CH:4][C:5]([N+:12]([O-:14])=[O:13])=[C:6]2[C:8]=1[C:17]([CH3:19])=[CH:15][CH:16]=[N:7]2

Participants

3

Reactant 2

HCID 6570Methyl vinyl ketoneHCID 46531524,5-Dimethoxy-2-nitroaniline

Product 1

HCID 6191084-Methyl-5,6-dimethoxy-8-nitroquinolineYield 27%

Procedure

A Skraup reaction of 4,5 -dimethoxy-2-nitroaniline with methyl vinyl ketone gave a 27% yield of 5,6-dimethoxy-4-methyl-8-nitroquinoline. The yellow compound crystallized well from methanol; mp 126°-127.5°.

Sources & evidence

ORD record
ord-661c5c8caa5b438888ef13e695849321
Source dataset
uspto-grants-1979_09
Patent number
US04167638

Reaction notes

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