Potassium Cyanide → 2-amino-3-phenyl-3H-indol-3-ol

HRID 1579526Notes

Reaction equation

HRID 1579526 reaction equation
[C:1]([C:9]1[CH:20]=[CH:19][CH:18]=[CH:17][C:10]=1[NH:11][C:12](=O)C(Cl)Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C-]#[N:22].[K+]>C(O)C.O>[NH2:22][C:12]1[C:1]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)([OH:8])[C:9]2[C:10](=[CH:17][CH:18]=[CH:19][CH:20]=2)[N:11]=1

Participants

5

Reactant 2

HCID 9032Potassium CyanideHCID 614210N-(2-Benzoylphenyl)-2,2-dichloroacetamide

Product 1

HCID 215687052-amino-3-phenyl-3H-indol-3-ol

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

2'-Benzoyl-2,2-dichloroacetanilide (50 g.) was suspended in 91% ethanol (750 ml) and treated with a solution of potassium cyanide (30 g) in water (50 ml). The reaction was stirred at room temperature for 40 hours. The crystalline precipitate was filtered off and the mother liquors diluted with water to provide further crops of 2-amino-3-phenyl-3H-indol-3-ol. Total 37 g. The product could be recrystallized from acetonitrile or aqueous dimethylformamide and had a m.p. of 204°-6°C (decomp).

Workup

  1. filtrationThe crystalline precipitate was filtered off
  2. additionthe mother liquors diluted with water

Sources & evidence

ORD record
ord-d4c057cab65e47fc8caa83a718bf18ae
Source dataset
uspto-grants-1976_01
Patent number
US03931226

Reaction notes

Loading…