HCID 66970310, compound → HCID 66970111, compound

HRID 1360018Notes

Reaction equation

HRID 1360018 reaction equation
[CH3:1][O:2][C:3](=[O:26])/[C:4](/[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[CH2:14][O:15][C:16]1[CH:21]=[CH:20][C:19]([N+:22]([O-])=O)=[CH:18][C:17]=1[F:25])=[CH:5]/[O:6][CH3:7].[H][H]>CO.C(OCC)(=O)C.[Pd]>[CH3:1][O:2][C:3](=[O:26])/[C:4](/[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[CH2:14][O:15][C:16]1[CH:21]=[CH:20][C:19]([NH2:22])=[CH:18][C:17]=1[F:25])=[CH:5]/[O:6][CH3:7]

Participants

6

Reactant 2

HCID 66970310HCID 66970310, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 66970111HCID 66970111, compoundYield 93.9%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

1.0 g (2.7 mmol) of the compound obtained in Step 1 was dissolved in a mixture of 5 ml of methanol and 5 ml of ethyl acetate, and 200 mg of 10% palladium/carbon was added thereto. The resulting mixture was placed in a hydrogenation reactor, and hydrogen gas was introduced therein with stirring the mixture for 18 hours. The reaction mixture was filtered through Cellite, and concentrated under a reduced pressure. The residue was subjected to column chromatography using 40% ethyl acetate/hexane as an eluent to obtain 0.84 g (yield 92%) of (E)-methyl-2-[2-((2-fluoro-4-aminophenoxy)methyl)phenyl]-3-methoxyacrylate.

Workup

  1. additionwas added
  2. customThe resulting mixture was placed in a hydrogenation reactor
  3. filtrationThe reaction mixture was filtered through Cellite
  4. concentrationconcentrated under a reduced pressure

Sources & evidence

ORD record
ord-21cf84fb431349b38731b847cc1af888
Source dataset
uspto-grants-2011_02
Patent number
US07879835B2

Reaction notes

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