N-(3-nitro-4-methylphenyl)-3-morpholinobenzamide → N-(3-amino-4-methylphenyl)-3-morpholinobenzamide

HRID 2302253Notes

Reaction equation

HRID 2302253 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([NH:11][C:12](=[O:25])[C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([N:19]3[CH2:24][CH2:23][O:22][CH2:21][CH2:20]3)[CH:14]=2)[CH:7]=[CH:8][C:9]=1[CH3:10])([O-])=O.[H][H]>CO.[Pd]>[NH2:1][C:4]1[CH:5]=[C:6]([NH:11][C:12](=[O:25])[C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([N:19]3[CH2:20][CH2:21][O:22][CH2:23][CH2:24]3)[CH:14]=2)[CH:7]=[CH:8][C:9]=1[CH3:10]

Participants

5

Reactant 2

HCID 22057949N-(3-nitro-4-methylphenyl)-3-morpholinobenzamideHCID 178418361HCID 178418361, compound2×

Product 1

HCID 11301391N-(3-amino-4-methylphenyl)-3-morpholinobenzamide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

10% Palladium-on-carbon (0.035 g) was added to a stirred solution in methanol (40 ml) of the nitro compound so obtained. (0.28 g) and the mixture was stirred at ambient temperature under 1 atmosphere pressure of hydrogen. After uptake of hydrogen had ceased, the catalyst was removed by filtration and the filtrate was evaporated to give N-(3-amino4-methylphenyl)-3-morpholinobenzamide; NMR Spectrum: (DMSOd6) 2.0 (s, 3H), 3.19 (t, 4H), 3.78 (t, 4H), 4.8 (s, 2H), 6.8 (q, 2H), 7.08 (s, 1H), 7.1 (d, 1H), 7.34 (m, 2H), 7.4 (s, 1H), 9.8 (s, 1H); Mass Spectrum: M+H+ 312.

Workup

  1. customso obtained
  2. customthe catalyst was removed by filtration
  3. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-6df6cf655ace47cf9d74c97feedfa571
Source dataset
uspto-grants-2002_08
Patent number
US06432949B1

Reaction notes

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