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

HRID 36928Notes

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

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

extractionextracted with ethyl acetate
washThe extract was washed with water
dry with materialdried (MgSO4)
distillationthe solvent was distilled off

Sources & evidence

ORD record: ord-47371527816841ddb6378dad826fb22b
Source dataset: uspto-grants-1995_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05418239

Reaction notes

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