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

HRID 1357699Notes

Reaction equation

HRID 1357699 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]>[Pd].C(O)C>[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, compound

Product 1

HCID 11301391N-(3-amino-4-methylphenyl)-3-morpholinobenzamideYield 79.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

10% palladium on carbon (150 mg) was added to a stirred suspension of N-(3-nitro-4-methylphenyl)-3-morpholinobenzamide (1.40 g) in ethanol (100 ml) under argon. The argon atmosphere was replaced with hydrogen and the mixture was stirred at ambient temperature for 4 hours. The catalyst was removed by filtration through diatomaceous earth (Celite®) and the residue washed with methylene chloride. The filtrate was evaporated to give a solid which was triturated with ethyl acetate to yield N-(3-amino-4-methylphenyl)-3-morpholinobenzamide (1.02 g); NMR: 2.0 (s, 3H), 3.19 (t, 4H), 3.78 (t, 4H), 4.8 (s, 2H), 6.8 (m, 2H), 7.08 (s, 1H), 7.11 (d, 1H), 7.34 (m, 2H), 7.4 (s, 1H), 9.8 (s, 1H); m/z 312.

Workup

  1. customThe catalyst was removed by filtration through diatomaceous earth (Celite®)
  2. washthe residue washed with methylene chloride
  3. customThe filtrate was evaporated
  4. customto give a solid which
  5. customwas triturated with ethyl acetate

Sources & evidence

ORD record
ord-cf53eb1fdb794a648cadd2bd07bd8b63
Source dataset
uspto-grants-2003_07
Patent number
US06593333B1

Reaction notes

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