N,N-Dimethylaniline → HCID 13588349, compound

HRID 1731380Notes

Reaction equation

HRID 1731380 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][CH:3]=1.Cl[C:10]1[C:18]([N+:19]([O-:21])=[O:20])=[CH:17][CH:16]=[C:15]([Cl:22])[C:11]=1[C:12]([OH:14])=[O:13].CN(C)C1C=CC=CC=1>CCOCC>[Cl:22][C:15]1[C:11]([C:12]([OH:14])=[O:13])=[C:10]([NH:1][C:2]2[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][CH:3]=2)[C:18]([N+:19]([O-:21])=[O:20])=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 949N,N-DimethylanilineHCID 7813p-ToluidineHCID 3506232,6-Dichloro-3-nitrobenzoic acid

Product 1

HCID 13588349HCID 13588349, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of 10.7 g of p-toluidine, 11.8 g of 2,6-dichloro-3-nitrobenzoic acid and 25 ml of N,N-dimethylaniline was stirred at 135° for 160 minutes. The mixture was diluted with ether and extracted with lN aqueous sodium hydroxide. Acidification of the aqueous solution, extraction with chloroform, and evaporation of the extract provided 6-chloro-2-[(4-methylphenyl)amino]-3-nitrobenzoic acid as orange prisms, mp 192°-197° C.

Workup

  1. extractionextracted with lN aqueous sodium hydroxide
  2. extractionAcidification of the aqueous solution, extraction
  3. customwith chloroform, and evaporation of the extract

Sources & evidence

ORD record
ord-7a3e6fb733c44f5aa1638034b039b916
Source dataset
uspto-grants-1986_11
Patent number
US04621086

Reaction notes

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