N,N-dimethyl-N-[2-(7-nitro-1H-indazol-4-yl)ethenyl]amine → 2-(7-nitro-1H-indazol-4-yl)acetonitrile

HRID 1032526

Reaction equation

HRID 1032526 reaction equation
C[N:2](C)[CH:3]=[CH:4][C:5]1[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[C:10]2[C:6]=1[CH:7]=[N:8][NH:9]2>O>[N+:14]([C:11]1[CH:12]=[CH:13][C:5]([CH2:4][C:3]#[N:2])=[C:6]2[C:10]=1[NH:9][N:8]=[CH:7]2)([O-:16])=[O:15]

Participants

3

Reactant 1

HCID 54098844N,N-dimethyl-N-[2-(7-nitro-1H-indazol-4-yl)ethenyl]amine

Product 1

HCID 136293082-(7-nitro-1H-indazol-4-yl)acetonitrileYield 78.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

At room temperature, 23.3 g of N,N-dimethyl-N-[2-(7-nitro-1H-indazol-4-yl)ethenyl]amine and 35.0 g of hydroxylamine-orthosulfonic acid are agitated in 400 ml of water for 24 hours. The precipitate is suctioned off, washed with water, and recrystallized from ethyl acetate, thus obtaining 16.0 g of 2-(7-nitro-1H-indazol-4-yl)acetonitrile, mp 198°-200° C.

Workup

  1. washwashed with water
  2. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-a29ec0adc9fb4b87a8123b7be4c25b04
Source dataset
uspto-grants-1990_09
Patent number
US04958026

Linked notes

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