3,3-Dimethyl-1-[2-nitro-4-(trifluoromethyl)phenyl]azetidin-2-one → 1-[2-Amino-4-(trifluoromethyl)phenyl]-3,3-dimethyl-2-azetidinone

HRID 1925403Notes

Reaction equation

HRID 1925403 reaction equation
[CH3:1][C:2]1([CH3:20])[CH2:5][N:4]([C:6]2[CH:11]=[CH:10][C:9]([C:12]([F:15])([F:14])[F:13])=[CH:8][C:7]=2[N+:16]([O-])=O)[C:3]1=[O:19]>CO.[Pd]>[NH2:16][C:7]1[CH:8]=[C:9]([C:12]([F:13])([F:14])[F:15])[CH:10]=[CH:11][C:6]=1[N:4]1[CH2:5][C:2]([CH3:1])([CH3:20])[C:3]1=[O:19]

Participants

4

Reactant 1

HCID 269856283,3-Dimethyl-1-[2-nitro-4-(trifluoromethyl)phenyl]azetidin-2-one

Product 1

HCID 160860981-[2-Amino-4-(trifluoromethyl)phenyl]-3,3-dimethyl-2-azetidinone

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 3,3-dimethyl-1-(2-nitro-4-(trifluoromethyl)phenyl)azetidin-2-one (1.67 g, 5.8 mmol, 1.0 equiv) and 10% Pd/C (300 mg) in MeOH (30 mL) was exposed to an atmosphere of H2. After consumption of the starting material, the mixture was filtered and concentrated to afford 1-(2-amino-4-(trifluoromethyl)phenyl-3,3-dimethylazetidin-2-one, which was advanced without further purification. MS (MH+) 259.1; Calculated 259.1 for C12H14F3N2O.

Workup

  1. customAfter consumption of the starting material
  2. filtrationthe mixture was filtered
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-c10628cf40484a0eb208125c48e93022
Source dataset
uspto-grants-2012_05
Patent number
US08178557B2

Reaction notes

Loading…