1-(3-Ethylamino-4-nitro-phenyl)-ethanone → 1-(4-Amino-3-ethylamino-phenyl)-ethanone

HRID 1594116Notes

Reaction equation

HRID 1594116 reaction equation
[CH2:1]([NH:3][C:4]1[CH:5]=[C:6]([C:13](=[O:15])[CH3:14])[CH:7]=[CH:8][C:9]=1[N+:10]([O-])=O)[CH3:2]>C(O)C.[Pd]>[NH2:10][C:9]1[CH:8]=[CH:7][C:6]([C:13](=[O:15])[CH3:14])=[CH:5][C:4]=1[NH:3][CH2:1][CH3:2]

Participants

4

Reactant 1

HCID 223800301-(3-Ethylamino-4-nitro-phenyl)-ethanone

Product 1

HCID 223800421-(4-Amino-3-ethylamino-phenyl)-ethanone

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

10% Pd/C (100 mg) is added to a Parr bottle containing 1-(3-ethylamino-4-nitro-phenyl)-ethanone (0.98 g, 4.7 mmol) in ethanol (40 mL). The Parr bottle is sealed in a mechanical shaker, evacuated, and then purged with nitrogen followed by hydrogen. The system is pressurized to 50 PSI of hydrogen at room temperature and mechanical shaking engaged. After 2 hours, shaking is stopped, and the system purged with nitrogen prior to opening the vessel. The reaction mixture is filtered through celite, concentrated in vacuo, to give 1-(4-amino-3-ethylamino-phenyl)-ethanone.

Workup

  1. customThe Parr bottle is sealed in a mechanical shaker
  2. customevacuated
  3. custompurged with nitrogen
  4. customis pressurized to 50 PSI of hydrogen at room temperature
  5. stirringshaking
  6. customthe system purged with nitrogen
  7. filtrationThe reaction mixture is filtered through celite
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2401aecd85534a52a024c5657098b20f
Source dataset
uspto-grants-2007_11
Patent number
US07300945B2

Reaction notes

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