N,N-Dimethylaniline → 2-(Bis(4-(dimethylamino)phenyl)methyl)-5-(dimethylamino)benzoic acid

HRID 434797Notes

Reaction equation

HRID 434797 reaction equation
[CH:1]([C:3]1[CH:11]=[CH:10][C:9]([N:12]([CH3:14])[CH3:13])=[CH:8][C:4]=1[C:5]([OH:7])=[O:6])=O.[CH3:15][N:16]([CH3:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>>[CH3:15][N:16]([CH3:23])[C:17]1[CH:22]=[CH:21][C:20]([CH:1]([C:3]2[CH:11]=[CH:10][C:9]([N:12]([CH3:14])[CH3:13])=[CH:8][CH:4]=2)[C:3]2[CH:11]=[CH:10][C:9]([N:12]([CH3:14])[CH3:13])=[CH:8][C:4]=2[C:5]([OH:7])=[O:6])=[CH:19][CH:18]=1

Participants

3

Reactant 2

HCID 949N,N-DimethylanilineHCID 147939725-(Dimethylamino)-2-formylbenzoic acid

Product 1

HCID 1020632-(Bis(4-(dimethylamino)phenyl)methyl)-5-(dimethylamino)benzoic acid

Procedure

In another known process for the preparation of CVL there are three steps. The first step comprises the interaction of the methyl ester of 2-formyl-5-dimethylaminobenzoic acid with two equivalents of N,N-dimethylaniline to obtain the methyl ester of 2-[bis(4-dimethylaminophenyl)-methyl]-5-dimethylaminobenzoic acid. After isolation, this benzoic acid is oxidized in the second step and finally in the third step the oxidized product is saponified and the lactone ring is closed to obtain the 3,3-bis(4-dimethylaminophenyl)-6-dimethylaminophthalide (CVL).

Workup

  1. customIn another known process for the preparation of CVL there

Sources & evidence

ORD record
ord-2aeb3ea4ce7a421c91c77ede6979987c
Source dataset
uspto-grants-1983_08
Patent number
US04399291

Reaction notes

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