2-Nitropropane → 5-methoxy-3-(2,2-dimethyl-2-nitroethyl)-1H-indole

HRID 2413034Notes

Reaction equation

HRID 2413034 reaction equation
CN([CH2:4][C:5]1[C:9]2[CH:10]=[C:11]([O:14][CH3:15])[CH:12]=[CH:13][C:8]=2[NH:7][CH:6]=1)C.[N+:16]([CH:19]([CH3:21])[CH3:20])([O-:18])=[O:17]>>[CH3:15][O:14][C:11]1[CH:10]=[C:9]2[C:8](=[CH:13][CH:12]=1)[NH:7][CH:6]=[C:5]2[CH2:4][C:19]([CH3:21])([N+:16]([O-:18])=[O:17])[CH3:20]

Participants

3

Reactant 2

HCID 3982-NitropropaneHCID 279655-Methoxy-N,N-dimethyl-1H-indole-3-methanamine

Product 1

HCID 126196625-methoxy-3-(2,2-dimethyl-2-nitroethyl)-1H-indole

Procedure

This material was prepared by the reaction of 5-methoxygramine (Procedure 11B) and 2-nitropropane substantially as described in Procedure 10C. The product was initially recovered as a dark oil which crystallized from i-Pr2O solution after treatment thereof with activated carbon, yield 31.3 g. (from 33 g. of 5-methoxygramine), m.p. 83°-85°. The identity of the product was confirmed by inspection of its NMR spectrum.

Workup

  1. customThe product was initially recovered as a dark oil which
  2. customcrystallized from i-Pr2O solution after treatment

Sources & evidence

ORD record
ord-3961d4c57a6742818b9fe5f8135a5555
Source dataset
uspto-grants-1985_01
Patent number
US04495352

Reaction notes

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