N,N-Dimethylaniline → HCID 13753447, compound

HRID 280254

Reaction equation

HRID 280254 reaction equation
[CH3:1][CH2:2][O:3][C:4]1[CH:5]=[CH:6][C:7]([NH2:10])=[CH:8][CH:9]=1.Cl[C:12]1[C:20]([N+:21]([O-:23])=[O:22])=[CH:19][CH:18]=[C:17]([Cl:24])[C:13]=1[C:14]([OH:16])=[O:15].CN(C)C1C=CC=CC=1>C(Cl)(Cl)Cl>[Cl:24][C:17]1[C:13]([C:14]([OH:16])=[O:15])=[C:12]([NH:10][C:7]2[CH:8]=[CH:9][C:4]([O:3][CH2:2][CH3:1])=[CH:5][CH:6]=2)[C:20]([N+:21]([O-:23])=[O:22])=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 949N,N-DimethylanilineHCID 90764-EthoxyanilineHCID 3506232,6-Dichloro-3-nitrobenzoic acid

Product 1

HCID 13753447HCID 13753447, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of 28.0 g of p-phenetidine, 23.6 g of 2,6-dichloro-3-nitrobenzoic acid, and 80 ml of N,N-dimethylaniline was heated five hours on a steam bath. The resulting mixture was diluted with chloroform and extracted with 1N sodium hydroxide. Acidification of the aqueous extract yielded 6-chloro-2-[(4-ethoxyphenyl)amino]-3-nitrobenzoic acid as reddish brown crystals.

Workup

  1. temperaturewas heated five hours on a steam bath
  2. extractionextracted with 1N sodium hydroxide
  3. extractionAcidification of the aqueous extract

Sources & evidence

ORD record
ord-f49559616c584729aba38e22075119ed
Source dataset
uspto-grants-1986_05
Patent number
US04588730

Linked notes

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