Hydrazine hydrate (1:1) → 4-chloro-5-methoxy-1H-indole

HRID 1898993Notes

Reaction equation

HRID 1898993 reaction equation
[N+]([C:4]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[C:13]([Cl:19])[C:5]=1[CH:6]=[CH:7][N:8]1CCCC1)([O-])=O.O.NN>C1C=CC=CC=1.[Ni]>[Cl:19][C:13]1[C:14]([O:17][CH3:18])=[CH:15][CH:16]=[C:4]2[C:5]=1[CH:6]=[CH:7][NH:8]2

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)2×HCID 542523322-Nitro-5-methoxy-6-chloro-beta-pyrrolidinostyrene

Product 1

HCID 233730984-chloro-5-methoxy-1H-indoleYield 83.9%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 241BenzeneSolvent

Procedure

A solution of 2-nitro-5-methoxy-6-chloro-β-pyrrolidinostyrene (5.28 g, 18.7 mmol) in benzene (100 ml) was stirred under nitrogen at 20° C. Raney nickel (0.50 ml) was added, followed by hydrazine hydrate (1.6 ml). After 30 minutes, more hydrazine hydrate was added (1.6 ml), and the mixture was stirred for a further 11/2 hours. After filtration through celite, the filtrate was evaporated to dryness to leave a dark yellow crystalline residue, which was purified by chromatography (SiO2 ; CHCl3), then recrystallised from benzene/hexane to give 4-chloro-5-methoxyindole (2.85 g) m.p. 112°-3° C.

Workup

  1. filtrationAfter filtration through celite
  2. customthe filtrate was evaporated to dryness
  3. customto leave a dark yellow crystalline residue, which
  4. customwas purified by chromatography (SiO2 ; CHCl3)
  5. customrecrystallised from benzene/hexane

Sources & evidence

ORD record
ord-aa5bec7b4743475b9b357066af4af07c
Source dataset
uspto-grants-1996_11
Patent number
US05571833

Reaction notes

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