HCID 21958891, compound → HCID 21958889, compound

HRID 1793422Notes

Reaction equation

HRID 1793422 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-eb55cb51d0694342836c240203e8b7f3
Source dataset
uspto-grants-2006_07
Patent number
US07081461B1

Reaction notes

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