Hydrazine hydrate (1:1) → Indole, 3-(2-amino-2-methylpropyl)-5-bromo-

HRID 224897

Reaction equation

HRID 224897 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[CH2:11][C:12]([CH3:17])([N+:14]([O-])=O)[CH3:13].O.NN>[Ni+2]>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[CH2:11][C:12]([CH3:17])([CH3:13])[NH2:14]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 126196615-Bromo-3-(2-methyl-2-nitropropyl)indole

Product 1

HCID 13259Indole, 3-(2-amino-2-methylpropyl)-5-bromo-

Reagents, catalysts & solvents 1

HCID 934Nickel cationCatalyst

Procedure

5-Bromo-3-(2-methyl-2-nitropropyl)indole, 5.9 g. was reduced with Raney nichel and hydrazine hydrate according to the method of Procedure 67D. The crude product was purified by dissolving in 200 ml. of dilute hydrochloric acid, treatment with activated charcoal, filtering, and basification of the filtrate with 10% aqueous sodium hydroxide. Yield 3.8 g. of white powder, m.p. 150°-155° C.

Workup

  1. customThe crude product was purified
  2. dissolutionby dissolving in 200 ml
  3. filtrationof dilute hydrochloric acid, treatment with activated charcoal, filtering

Sources & evidence

ORD record
ord-1e15576f9e24402ea73d6f066ceafe14
Source dataset
uspto-grants-1980_11
Patent number
US04234595

Linked notes

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