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

HRID 1982294Notes

Reaction equation

HRID 1982294 reaction equation
[CH3:1][N:2]([CH3:9])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH3:10][N:11]([CH3:31])[C:12]1[CH:17]=[CH:16][C:15]([CH:18]2[C:27]3[C:22](=[CH:23][C:24]([N:28]([CH3:30])[CH3:29])=[CH:25][CH:26]=3)[C:20](=[O:21])[O:19]2)=[CH:14][CH:13]=1>[Cl-].[Zn+2].[Cl-]>[CH3:1][N:2]([CH3:9])[C:3]1[CH:8]=[CH:7][C:6]([CH:18]([C:27]2[CH:26]=[CH:25][C:24]([N:28]([CH3:29])[CH3:30])=[CH:23][C:22]=2[C:20]([OH:21])=[O:19])[C:15]2[CH:14]=[CH:13][C:12]([N:11]([CH3:10])[CH3:31])=[CH:17][CH:16]=2)=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 949N,N-DimethylanilineHCID 936931(3H)-Isobenzofuranone, 6-(dimethylamino)-3-[4-(dimethylamino)phenyl]-

Product 1

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

Reagents, catalysts & solvents 1

HCID 3007855ZincchlorideCatalyst

Procedure

Following a procedure similar to that described in part A above, but substituting 18.2 g of anhydrous stannic chloride for the anhydrous zinc chloride, 70.0 ml of N,N-dimethylaniline and 14.9 g of 3-(4-dimethylaminophenyl)-6-dimethylaminophthalide prepared as described in Example 1, part A above were interacted to obtain 15.0 g of 2-[4,4'-bis(dimethylamino)-benzhydryl]-5-dimethylaminobenzoic acid which melted at 208°-212° C.

Workup

  1. customprepared

Sources & evidence

ORD record
ord-95efe58a89dc426aacc0e8808022613c
Source dataset
uspto-grants-1986_06
Patent number
US04595768

Reaction notes

Loading…