Ammonia → 5-Amino-6-(2-chlorobenzoyl)indan

HRID 258035Notes

Reaction equation

HRID 258035 reaction equation
[Cl:1][C:2]1[CH:28]=[CH:27][CH:26]=[CH:25][C:3]=1[C:4]([C:6]1[CH:14]=[C:13]2[C:9]([CH2:10][CH2:11][CH2:12]2)=[CH:8][C:7]=1[NH:15]C(=O)C1C=CC=CC=1Cl)=[O:5].N>OS(O)(=O)=O>[NH2:15][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][C:6]=1[C:4](=[O:5])[C:3]1[CH:25]=[CH:26][CH:27]=[CH:28][C:2]=1[Cl:1])[CH2:12][CH2:11][CH2:10]2

Participants

4

Reactant 2

HCID 222AmmoniaHCID 199365836-(2-Chlorobenzoyl)-5-(2-chlorobenzoylamino)indan

Product 1

HCID 199365705-Amino-6-(2-chlorobenzoyl)indanYield 94.4%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 6-(2-chlorobenzoyl)-5-(2-chlorobenzoylamino)indan (16.0 g) and 70% H2SO4 (100 ml) was heated at 120° C. for 30 minutes and, then, poured in ice-water (300 ml). The solution was alkalinized with concentrated aqueous ammonia and extracted with ethyl acetate. The extract was washed with water and dried (MgSO4) and the solvent was distilled off to give 5-amino-6-(2-chlorobenzoyl)indan as yellow oil (10.0 g, 94.3%). Recrystallization from hexane gave yellow prisms, m.p. 90°-92°.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with water
  3. dry with materialdried (MgSO4)
  4. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-389b189ce1a043b99d94f04826163a08
Source dataset
uspto-grants-1993_11
Patent number
US05264454

Reaction notes

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