Sodium Hydroxide → 2-phenyl-1H-indol-3-amine

HRID 746818Notes

Reaction equation

HRID 746818 reaction equation
[N:1]([C:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[NH:5][C:4]=1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=O.[OH-].[Na+].S(S([O-])=O)([O-])=O.[Na+].[Na+]>C(O)C>[NH2:1][C:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[NH:5][C:4]=1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 24489Sodium DithioniteHCID 3439763-Nitroso-2-phenyl-1H-indole

Product 1

HCID 27493402-phenyl-1H-indol-3-amine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 3-nitroso-2-phenyl indole (28) (25 gm, 0.129 mol) in ethanol (450 ml) was added 2N sodium hydroxide (300 mL, 5.0 eq) followed by sodium dithionite (38 g). The reaction was heated at reflux for 5 h, then filtered. The solid was washed with water and dried under vacuum to provide Compound 29 as a yellow solid. Yield=15 g (72.1%). ES-MS: 209.25 (M++1); NMR (DMSO-d6): 7.0 (m, 1H), 7.1 (m, 1H), 7.22 (m, 1H), 7.32 (m, 2H), 7.40 (m, 1H), 7.48 (m, 2H), 7.60 (m, 1H).

Workup

  1. temperatureThe reaction was heated
  2. temperatureat reflux for 5 h
  3. filtrationfiltered
  4. washThe solid was washed with water
  5. customdried under vacuum

Sources & evidence

ORD record
ord-6f7094c3f70e47c8b959d1b7a0cbfc57
Source dataset
uspto-grants-2008_07
Patent number
US07393955B2

Reaction notes

Loading…