Ammonia → 5-Chloro-2-(1H-tetrazol-1-yl)benzenemethanamine

HRID 857718Notes

Reaction equation

HRID 857718 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:10]2[CH:14]=[N:13][N:12]=[N:11]2)=[C:6]([CH:9]=1)[C:7]#[N:8].N>C(O)C.[Ni]>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:10]2[CH:14]=[N:13][N:12]=[N:11]2)=[C:6]([CH:9]=1)[CH2:7][NH2:8]

Participants

5

Reactant 2

HCID 222AmmoniaHCID 218662805-Chloro-2-(1H-tetrazol-1-YL)benzonitrile

Product 1

HCID 113217565-Chloro-2-(1H-tetrazol-1-yl)benzenemethanamineYield 50.3%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

A solution of 5-chloro-2-(1H-tetraazol-1-yl)benzonitrile (113 mg, 0.55 mmol) in ethanol saturated with ammonia (20 mL) was stirred in the presence of Raney nickel (50% slurry in water, washed with ethanol, catalytic amount) under a hydrogen atmosphere for 1 h. The reaction mixture was filtered through Celite and concentrated to give 5-chloro-2-tetrazol-1-yl-benzylamine (58 mg, 50%); 1H NMR (400 MHz, CDCl3): δ 9.24 (s, 1H), 7.64 (d, J=2.2 Hz, 1H), 7.46 (m, 1H), 7.38 (m, 1H), 3.68 (s, 2H).

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-836f5b0934294f70ace4d27120bf44de
Source dataset
uspto-grants-2006_12
Patent number
US07144899B2

Reaction notes

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