2-(7-nitro-1H-indazol-4-yl)acetonitrile → 2-(7-amino-1H-indazol-4-yl)acetonitrile

HRID 1032544

Reaction equation

HRID 1032544 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([CH2:13][C:14]#[N:15])=[C:8]2[C:12]=1[NH:11][N:10]=[CH:9]2)([O-])=O>O1CCCC1.[Ni]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([CH2:13][C:14]#[N:15])=[C:8]2[C:12]=1[NH:11][N:10]=[CH:9]2

Participants

4

Reactant 1

HCID 136293082-(7-nitro-1H-indazol-4-yl)acetonitrile

Product 1

HCID 193544342-(7-amino-1H-indazol-4-yl)acetonitrileYield 87.8%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8028TetrahydrofuranSolvent

Procedure

20.2 g of 2-(7-nitro-1H-indazol-4-yl)-acetonitrile in 750 ml of tetrahydrofuran is hydrogenated in the presence of 20.0 g of Raney nickel. The product is recrystallized from tetrahydrofuran/hexane, yielding 15.1 g of 2-(7-amino-1H-indazol-4-yl)acetonitrile, mp 164°-165° C.

Workup

  1. customThe product is recrystallized from tetrahydrofuran/hexane

Sources & evidence

ORD record
ord-eb4a0d8baa674734875fca2f76128da7
Source dataset
uspto-grants-1990_09
Patent number
US04958026

Linked notes

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