4-Methoxy-benzofuran-3-one oxime → 4-Methoxy-2,3-dihydrobenzofuran-3-amine

HRID 1931524Notes

Reaction equation

HRID 1931524 reaction equation
[CH3:1][O:2][C:3]1[C:8]2[C:9](=[N:12]O)[CH2:10][O:11][C:7]=2[CH:6]=[CH:5][CH:4]=1>C(O)C.[Pd]>[CH3:1][O:2][C:3]1[C:8]2[CH:9]([NH2:12])[CH2:10][O:11][C:7]=2[CH:6]=[CH:5][CH:4]=1

Participants

4

Reactant 1

HCID 866341844-Methoxy-benzofuran-3-one oxime

Product 1

HCID 672125224-Methoxy-2,3-dihydrobenzofuran-3-amineYield 64.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of the above described 4-methoxy-benzofuran-3-one oxime (6.15 g, 34.3 mmol) in ethanol (500 ml) with 10% palladium on charcoal (6.15 g) was hydrogenated at 23° C. and atmospheric pressure for 18 h. Filtered the catalyst off, washed with ethanol, evaporated the filtrate totally and dried in high vacuum to give rac-4-methoxy-2,3-dihydro-benzofuran-3-ylamine as a light yellow oil (3.65 g, 64%); MS: m/e=166.2 (M+H+).

Workup

  1. additionA mixture of the
  2. customwas hydrogenated at 23° C.
  3. filtrationFiltered the catalyst off,
  4. washwashed with ethanol
  5. customevaporated the filtrate totally
  6. customdried in high vacuum

Sources & evidence

ORD record
ord-bd8b56bbfe7047ba9f313a0135c718b8
Source dataset
uspto-grants-2012_05
Patent number
US08188284B2

Reaction notes

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