HCID 21958891, compound → HCID 21958889, compound

HRID 2213866Notes

Reaction equation

HRID 2213866 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]([N+:20]([O-])=O)=[CH:12][C:13]=1[O:14][CH2:15][C:16]([F:19])([F:18])[F:17])[C:6]([O:8][CH2:9][CH3:10])=[O:7]>[Pd].C(O)C.C(OCC)(=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]([NH2:20])=[CH:12][C:13]=1[O:14][CH2:15][C:16]([F:18])([F:17])[F:19])[C:6]([O:8][CH2:9][CH3:10])=[O:7]

Participants

5

Reactant 1

HCID 21958891HCID 21958891, compound

Product 1

HCID 21958889HCID 21958889, compoundYield 93%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A suspension of ethyl 3-methoxy-4-(2,2,2-trifluoroethoxy)-6-nitrobenzoate (24.0 g, 74.3 mmol) and 10% palladium on carbon (3.0 g) in a mixture of ethanol (100 ml) and ethyl acetate (750 ml) was stirred under an atmosphere of hydrogen for 18 hours. Removal of the catalyst by filtration, followed by solvent evaporation in vacuo yielded ethyl 3-methoxy-4-(2,2,2-trifluoroethoxy)-6-aminobenzoate (20.2 g, 93% yield) as a pale brown solid:

Workup

  1. customRemoval of the catalyst
  2. filtrationby filtration
  3. customfollowed by solvent evaporation in vacuo

Sources & evidence

ORD record
ord-3c961328e4894a24a79de734a2ae8363
Source dataset
uspto-grants-2006_09
Patent number
US07105669B1

Reaction notes

Loading…