2-Azido-1-(3-(trifluoromethoxy)phenyl)ethanone → 2-Amino-1-(3-(trifluoromethoxy)phenyl)ethanone

HRID 419696Notes

Reaction equation

HRID 419696 reaction equation
[N:1]([CH2:4][C:5]([C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([O:13][C:14]([F:17])([F:16])[F:15])[CH:8]=1)=[O:6])=[N+]=[N-]>[Pd].C(O)C>[NH2:1][CH2:4][C:5]([C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([O:13][C:14]([F:15])([F:16])[F:17])[CH:8]=1)=[O:6]

Participants

4

Reactant 1

HCID 866320132-Azido-1-(3-(trifluoromethoxy)phenyl)ethanone

Product 1

HCID 666499302-Amino-1-(3-(trifluoromethoxy)phenyl)ethanoneYield 102.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Add palladium on carbon (720 mg, 10% Pd/C, 50% water by weight) to a nitrogen purged solution of 2-azido-1-(3-(trifluoromethoxy)phenyl)ethanone (1.70 g, 6.93 mmol) in ethanol (15 mL). Purge the flask with hydrogen (balloon). Stir at room temperature overnight. Filter the mixture over Celite®, rinse the Celite® with ethanol (3×30 mL), and concentrate the filtrate in vacuo to provide crude 2-amino-1-(3-(trifluoromethoxy)phenyl)ethanone (1.56 g, 88%). 1H NMR (DMSO-d6) δ 8.56 (br s, 2H), 8.07 (m, 1H), 7.95 (s, 1H), 7.76 (m, 2H), 4.63 (s, 2H).

Workup

  1. customPurge the flask with hydrogen (balloon)
  2. filtrationFilter the mixture over Celite®
  3. washrinse the Celite® with ethanol (3×30 mL)
  4. concentrationconcentrate the filtrate in vacuo

Sources & evidence

ORD record
ord-03504a7c07b34b5faeed2379ae1a668d
Source dataset
uspto-grants-2012_01
Patent number
US08093383B2

Reaction notes

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