Ammonium formate → HCID 59410068, compound

HRID 2404853Notes

Reaction equation

HRID 2404853 reaction equation
[CH:1]1([C:7]2[CH:12]=[CH:11][C:10]([NH:13][C:14](=[O:16])[CH3:15])=[CH:9][C:8]=2[N+:17]([O-])=O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C([O-])=O.[NH4+]>C(O)C.[Pd]>[NH2:17][C:8]1[CH:9]=[C:10]([NH:13][C:14](=[O:16])[CH3:15])[CH:11]=[CH:12][C:7]=1[CH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 59410103HCID 59410103, compound

Product 1

HCID 59410068HCID 59410068, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a refluxing solution of N-(4-cyclohexyl-3-nitro-phenyl)acetamide (1.8 g, 6.86 mmol) and ammonium formate (1.8 g, 28.55 mmol) in ethanol (50 mL) was added 10% Pd/C (1.3 g, 12.22 mmol). The mixture was refluxed for additional 5 minutes, cooled and filtered through a pad of celite. The solvent was removed by evaporation to give N-(3-amino-4-cyclohexylphenyl)acetamide (1.4 g, 90%) which was used without further purification. 1H NMR (400 MHz, CDCl3) δ 7.15 (d, J=2.1 Hz, 2H), 7.03 (d, J=8.3 Hz, 1H), 6.67 (dd, J=8.2, 2.1 Hz, 1H), 3.72 (d, J=9.8 Hz, 2H), 2.42 (d, J=8.5 Hz, 1H), 2.15 (s, 3H), 1.88 (d, J=9.5 Hz, 4H), 1.78 (d, J=12.1 Hz, 1H), 1.51-1.33 (m, 5H).

Workup

  1. temperatureThe mixture was refluxed for additional 5 minutes
  2. temperaturecooled
  3. filtrationfiltered through a pad of celite
  4. customThe solvent was removed by evaporation

Sources & evidence

ORD record
ord-87d193b0db674b82badba5ef16d597ef
Source dataset
uspto-grants-2014_08
Patent number
US08802700B2

Reaction notes

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