N-(2-Amino-4-chlorophenyl)anthranilic acid → 8-chloro-5,10-dihydro-11H-dibenzo[b,e][1,4]diazepin-11-one

HRID 16190

Reaction equation

HRID 16190 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10]1[CH:18]=[CH:17][CH:16]=[CH:15][C:11]=1[C:12](O)=[O:13]>C1(C)C(C)=CC=CC=1>[Cl:8][C:6]1[CH:5]=[CH:4][C:3]2[NH:9][C:10]3[CH:18]=[CH:17][CH:16]=[CH:15][C:11]=3[C:12](=[O:13])[NH:1][C:2]=2[CH:7]=1

Participants

3

Reactant 1

HCID 610730N-(2-Amino-4-chlorophenyl)anthranilic acid

Product 1

HCID 36531168-chloro-5,10-dihydro-11H-dibenzo[b,e][1,4]diazepin-11-one

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A solution of 2-[(2-amino-4-chlorophenyl)amino]benzoic acid (11.8 g, 45 mmol) in xylene (150 mL) was heated to reflux in a Dean-Stark apparatus. The reaction mixture was stirred at reflux temperature for 31 h. After removal of the xylene in vacuo, the title compound was obtained. There was still starting material present. Therefore the product was dissolved in xylene (150 mL) again and stirring was continued overnight at reflux temperature in a Dean-Stark apparatus. After removal of the xylene under reduced pressure the title compound (12.4 g, 50.6 mmol) was obtained.

Workup

  1. temperatureto reflux in a Dean-Stark apparatus
  2. temperatureat reflux temperature for 31 h
  3. customAfter removal of the xylene in vacuo

Sources & evidence

ORD record
ord-ead65bc416034178bfb8f49ceb9eaf1f
Source dataset
uspto-grants-2010_06
Patent number
US07737136B2

Linked notes

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