N,N-Dimethylaniline → HCID 13651738, compound

HRID 1982296Notes

Reaction equation

HRID 1982296 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[C:18]3[C:13](=[CH:14][C:15]([N:19]([CH3:21])[CH3:20])=[CH:16][CH:17]=3)[C:11](=[O:12])[O:10]2)=[CH:5][CH:4]=1.[CH3:22][N:23]([CH3:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>[Cl-].[Zn+2].[Cl-]>[CH3:22][N:23]([CH3:30])[C:24]1[CH:29]=[CH:28][C:27]([CH:9]([C:18]2[CH:17]=[CH:16][C:15]([N:19]([CH3:21])[CH3:20])=[CH:14][C:13]=2[C:11]([OH:10])=[O:12])[C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)=[CH:26][CH:25]=1

Participants

4

Reactant 2

HCID 949N,N-DimethylanilineHCID 123896946-(Dimethylamino)-3-(4-methoxyphenyl)-2-benzofuran-1(3H)-one

Product 1

HCID 13651738HCID 13651738, compound

Reagents, catalysts & solvents 1

HCID 3007855ZincchlorideCatalyst

Procedure

Following the procedure described in Example 26, part A, 9.9 g of 3-(4-methoxyphenyl)-6-dimethylaminophthalide, prepared as described in Example 12, part A above, and 89.0 ml of N,N-dimethylaniline were interacted in the presence of 9.5 g of anhydrous zinc chloride at room temperature to obtain 13.7 g of 2-(4-dimethylamino-4'-methoxybenzhydryl)-5-dimethylaminobenzoic acid as an off-white colored solid melting at 185°-190° C.

Workup

  1. customprepared

Sources & evidence

ORD record
ord-26bf26daaf634c8a82da03d4fa42d4a4
Source dataset
uspto-grants-1986_06
Patent number
US04595768

Reaction notes

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