N,N-Dimethylaniline → HCID 54570148, compound

HRID 1459663Notes

Reaction equation

HRID 1459663 reaction equation
[CH2:1]([O:8][C:9]1[CH:15]=[CH:14][C:12]([NH2:13])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[C:17]1[C:25]([N+:26]([O-:28])=[O:27])=[CH:24][CH:23]=[CH:22][C:18]=1[C:19]([OH:21])=[O:20].CN(C)C1C=CC=CC=1.C(N(CC)C(C)C)(C)C.[OH-].[Na+]>C(Cl)(Cl)Cl>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([NH:13][C:17]2[C:25]([N+:26]([O-:28])=[O:27])=[CH:24][CH:23]=[CH:22][C:18]=2[C:19]([OH:21])=[O:20])=[CH:14][CH:15]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 5

HCID 949N,N-DimethylanilineHCID 14798Sodium HydroxideHCID 198702-Chloro-3-nitrobenzoic acidHCID 228604-BenzyloxyanilineHCID 81531Diisopropylethylamine

Product 1

HCID 54570148HCID 54570148, compoundYield 90.6%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture comprising 2.2 g (11 mmol.) of 4-benzyloxyaniline, 2.0 g (10 mmol) of 2-chloro-3-nitrobenzoic acid, 6 ml of N,N-dimethylaniline and 1.6 ml of N,N-diisopropylethylamine was heated at 100° C. for 12 hours under stirring. After cooling, 30 ml, of chloroform and 30 ml of 1N sodium hydroxide were added thereto. The precipitate thus formed was separated by filtration, stirred together with 5% hydrochloric acid and washed with water to thereby give 3.3 g of 2-((4-benzyloxyphenyl)amino)-3-nitrobenzoic acid. This product was added to 40 ml of chloroform and 0.3 ml of N,N-dimethylaniline and 6 ml of phosphorus oxychloride were further added thereto. After heating under reflux for 30 minutes and then cooling, the crystals thus precipitated were separated by filtration. Thus 2.1 g of the title compound was obtained.

Workup

  1. temperatureAfter cooling
  2. customThe precipitate thus formed
  3. customwas separated by filtration
  4. stirringstirred together with 5% hydrochloric acid
  5. washwashed with water

Sources & evidence

ORD record
ord-1ca496fd0b904cd2b562134e34e72926
Source dataset
uspto-grants-1998_12
Patent number
US05854274

Reaction notes

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