Aniline → 3-Phenylaminomethylene-6,7-dimethoxy-2-methyl-4-oxo-1,2,3,4-tetrahydro-1-quinoline carboxylic acid, ethyl ester

HRID 328809Notes

Reaction equation

HRID 328809 reaction equation
[CH2:1]([O:3][C:4]([N:6]1[C:15]2[C:10](=[CH:11][C:12]([O:18][CH3:19])=[C:13]([O:16][CH3:17])[CH:14]=2)[C:9](=[O:20])[C:8](=[CH:21]O)[CH:7]1[CH3:23])=[O:5])[CH3:2].[NH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>C1C=CC=CC=1>[C:25]1([NH:24][CH:21]=[C:8]2[C:9](=[O:20])[C:10]3[C:15](=[CH:14][C:13]([O:16][CH3:17])=[C:12]([O:18][CH3:19])[CH:11]=3)[N:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])[CH:7]2[CH3:23])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

4

Reactant 2

HCID 6115AnilineHCID 70638946Racemic Ethyl 6,7-Dimethoxy-3-hydroxymethylene-2-methyl-4-oxo-1,2,3,4-tetrahydroquinoline-1-carboxylate

Product 1

HCID 867338923-Phenylaminomethylene-6,7-dimethoxy-2-methyl-4-oxo-1,2,3,4-tetrahydro-1-quinoline carboxylic acid, ethyl ester

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Starting with 3.2 g. of 3-hydroxymethylene-6,7-dimethoxy-2-methyl-4-oxo-1,2,3,4-tetrahydro-1-quinoline carboxylic acid ethyl ester and 1.0 g. an aniline in 30 ml. of benzene and employing the reaction procedures of Example 5 provides 3.2 g. of the desired product as a yellow oil.

Workup

  1. customthe reaction procedures of Example 5
  2. customprovides 3.2 g

Sources & evidence

ORD record
ord-edab388b93464c62811f35200c16b7b3
Source dataset
uspto-grants-1977_04
Patent number
US04018758

Reaction notes

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