N-(2-morpholinoethyl)-3-nitro-5-(trifluoromethyl)benzamide → 3-amino-N-(2-morpholinoethyl)-5-(trifluoromethyl)benzamide

HRID 1042691Notes

Reaction equation

HRID 1042691 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([CH2:7][CH2:8][NH:9][C:10](=[O:24])[C:11]2[CH:16]=[C:15]([C:17]([F:20])([F:19])[F:18])[CH:14]=[C:13]([N+:21]([O-])=O)[CH:12]=2)[CH2:3][CH2:2]1>CCOC(C)=O.CO.[Pd]>[NH2:21][C:13]1[CH:12]=[C:11]([CH:16]=[C:15]([C:17]([F:20])([F:19])[F:18])[CH:14]=1)[C:10]([NH:9][CH2:8][CH2:7][N:4]1[CH2:3][CH2:2][O:1][CH2:6][CH2:5]1)=[O:24]

Participants

5

Reactant 1

HCID 59427894N-(2-morpholinoethyl)-3-nitro-5-(trifluoromethyl)benzamide

Product 1

HCID 594279303-amino-N-(2-morpholinoethyl)-5-(trifluoromethyl)benzamide

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of N-(2-morpholinoethyl)-3-nitro-5-(trifluoromethyl)benzamide (300 mg, 0.865 mmol, 1.0 equiv) and 10% Pd/C (20 mg) in EtOAc (25 ml) and MeOH (2 mL) was exposed to an atmosphere of H2 (balloon). Upon completion of the reduction, the reaction mixture was filtered through celite and concentrated in vacuo to afford 3-amino-N-(2-morpholinoethyl)-5-(trifluoromethyl)benzamide, which was advanced without further purification. MS m/z: 318 (M+H+); Calculated for C14H18F3N3O2: 317.1

Workup

  1. filtrationUpon completion of the reduction, the reaction mixture was filtered through celite and
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d5b69e563ad94a5394b882a588a6cf93
Source dataset
uspto-grants-2013_10
Patent number
US08557996B2

Reaction notes

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