3-ethoxy-N-ethyl-4-nitrobenzamide → 4-amino-3-ethoxy-N-ethylbenzamide

HRID 1717329Notes

Reaction equation

HRID 1717329 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:12]=[CH:13][C:14]=1[N+:15]([O-])=O)[C:7]([NH:9][CH2:10][CH3:11])=[O:8])[CH3:2]>C(O)C.[Pd]>[NH2:15][C:14]1[CH:13]=[CH:12][C:6]([C:7]([NH:9][CH2:10][CH3:11])=[O:8])=[CH:5][C:4]=1[O:3][CH2:1][CH3:2]

Participants

4

Reactant 1

HCID 685151263-ethoxy-N-ethyl-4-nitrobenzamide

Product 1

HCID 633585494-amino-3-ethoxy-N-ethylbenzamideYield 84.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 3-ethoxy-N-ethyl-4-nitrobenzamide (0.72 g) obtained in Example 131b) in ethanol (15 ml) was added 10% Pd/C (50% wet) (0.07 g), and the mixture was stirred at room temperature overnight under a hydrogen atmosphere. The reaction mixture was filtered through celite, and the filtrate was evaporated under reduced pressure. The residue was purified by silica gel column (ethyl acetate/hexane=1/1 to ethyl acetate) to give the title compound as a colorless oil (0.53 g, 84%).

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. customthe filtrate was evaporated under reduced pressure
  3. customThe residue was purified by silica gel column (ethyl acetate/hexane=1/1 to ethyl acetate)

Sources & evidence

ORD record
ord-59560237a5f747348f8504953d8f599d
Source dataset
uspto-grants-2010_09
Patent number
US07803822B2

Reaction notes

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