4-Methyl-3-nitro-N-phenylbenzene-1-carboximidic acid → 3-Amino-4-methyl-N-phenylbenzamide

HRID 1859645Notes

Reaction equation

HRID 1859645 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:16]=[CH:17][C:18]=1[CH3:19])[C:7]([NH:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:8])([O-])=O.[H][H]>[Ni].O1CCCC1.CO>[NH2:1][C:4]1[CH:5]=[C:6]([CH:16]=[CH:17][C:18]=1[CH3:19])[C:7]([NH:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:8]

Participants

6

Reactant 2

HCID 7964134-Methyl-3-nitro-N-phenylbenzene-1-carboximidic acidHCID 178418361HCID 178418361, compound

Product 1

HCID 126079813-Amino-4-methyl-N-phenylbenzamideYield 101.3%

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Raney nickel (1 g) was added to a solution of 3-nitro-4-methyl-N-phenyl-benzamide (6.2 g, 24 mmol) in a mixture of tetrahydro-furan (50 mL) and methanol (100 mL) and shaken at room temperature under an atmosphere of hydrogen, initially at a pressure of 50 psi, until the required amount of hydrogen was taken up. The catalyst was removed by filtration, and the filtrate was stripped of solvent by rotary evaporator. The residue was dried under reduced pressure to afford the pure product (5.5 g); m.p. 149-151° C.

Workup

  1. customThe catalyst was removed by filtration
  2. customthe filtrate was stripped of solvent by rotary evaporator
  3. customThe residue was dried under reduced pressure

Sources & evidence

ORD record
ord-9bc0f0240c2440f5bb600838c0c7c9ea
Source dataset
uspto-grants-2003_03
Patent number
US06528528B2

Reaction notes

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