Methyl vinyl ketone → 4-Methyl-5-fluoro-6-methoxy-8-nitroquinoline

HRID 1863119Notes

Reaction equation

HRID 1863119 reaction equation
[NH2:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][C:5]([O:11][CH3:12])=[C:4]([F:13])[CH:3]=1.[CH:14]([C:16]([CH3:18])=O)=[CH2:15]>>[F:13][C:4]1[C:5]([O:11][CH3:12])=[CH:6][C:7]([N+:8]([O-:10])=[O:9])=[C:2]2[C:3]=1[C:16]([CH3:18])=[CH:14][CH:15]=[N:1]2

Participants

3

Reactant 2

HCID 6570Methyl vinyl ketoneHCID 2196205-Fluoro-4-methoxy-2-nitroaniline

Product 1

HCID 126110024-Methyl-5-fluoro-6-methoxy-8-nitroquinolineYield 32%

Procedure

The intermediate 4-amino-2-fluoro-5-nitroanisole and methyl vinyl ketone were subjected to a Skraup reaction. A 32% yield of crude 5-fluoro-6-methoxy-4-methyl-8-nitroquinoline resulted. It was obtained in pure form by recrystallization from ethyl acetate. The recovery was 73% of product which melted 142°-144°.

Sources & evidence

ORD record
ord-adeb2d79a65d49638f949be8b353fe0d
Source dataset
uspto-grants-1979_09
Patent number
US04167638

Reaction notes

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