Ammonia → 2-amino-4-[(1H-imidazol-1-yl)phenylmethyl]benzamide

HRID 2247899Notes

Reaction equation

HRID 2247899 reaction equation
[N:1]1([CH:6]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:7]2[CH:14]=[CH:13][C:10]([C:11]#[N:12])=[C:9]([N+:15]([O-])=O)[CH:8]=2)[CH:5]=[CH:4][N:3]=[CH:2]1.N.[H][H].C[OH:28]>[Ni]>[NH2:15][C:9]1[CH:8]=[C:7]([CH:6]([N:1]2[CH:5]=[CH:4][N:3]=[CH:2]2)[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:14]=[CH:13][C:10]=1[C:11]([NH2:12])=[O:28]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 887MethanolHCID 54537560HCID 54537560, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 538753582-amino-4-[(1H-imidazol-1-yl)phenylmethyl]benzamideYield 82.9%

Reagents, catalysts & solvents 1

HCID 935NickelCatalyst

Procedure

A solution of 6 parts of intermediate 52, namely 4-[(1H-imidazol-1-yl)phenylmethyl]-2-nitrobenzonitrile, in 316 parts of methanol saturated with ammonia was hydrogenated at room temperature and normal pressure with 3 parts of Raney nickel. After the calculated amount of hydrogen was taken up, the catalyst was filtered off and the filtrate was evaporated. The residue was co-evaporated with a mixture of methanol and methylbenzene, yielding 4.8 parts (82.9%) of 2-amino-4-[(1H-imidazol-1-yl)phenylmethyl]benzamide (interm. 53).

Workup

  1. customwas hydrogenated at room temperature
  2. filtrationthe catalyst was filtered off
  3. customthe filtrate was evaporated
  4. additionThe residue was co-evaporated with a mixture of methanol and methylbenzene

Sources & evidence

ORD record
ord-e215ab479ba8457085a640e979620319
Source dataset
uspto-grants-1991_08
Patent number
US05037829

Reaction notes

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