4-Methoxy-2-nitroaniline → HCID 178493297, compound

HRID 1863100Notes

Reaction equation

HRID 1863100 reaction equation
[CH3:1][O:2][C:3]1[CH:9]=[CH:8][C:6]([NH2:7])=[C:5]([N+:10]([O-:12])=[O:11])[CH:4]=1.[F:13][C:14]([F:24])([F:23])[C:15](=O)[CH2:16][C:17](OCC)=[O:18]>>[OH:18][C:17]1[C:8]2[C:6](=[C:5]([N+:10]([O-:12])=[O:11])[CH:4]=[C:3]([O:2][CH3:1])[CH:9]=2)[N:7]=[C:15]([C:14]([F:24])([F:23])[F:13])[CH:16]=1

Participants

3

Reactant 2

HCID 667934-Methoxy-2-nitroanilineHCID 67793Ethyl 4,4,4-trifluoroacetoacetate

Product 1

HCID 178493297HCID 178493297, compoundYield 27%

Procedure

The reaction of 4-methoxy-2-nitroaniline with ethyl trifluoroacetoacetate in polyphosphoric acid at 130°-140° gave 4-hydroxy-6-methoxy-8-nitro-2-trifluoromethylquinoline. The pure compound (tan crystals, mp 138°-140° ) was obtained in 27% yield following several crystallizations of the crude product from ligroin.

Sources & evidence

ORD record
ord-5253d612d88a4a53be0e4e6c1c20af15
Source dataset
uspto-grants-1979_09
Patent number
US04167638

Reaction notes

Loading…