4-Ethoxy-benzofuran-3-one oxime → 4-Ethoxy-2,3-dihydro-3-benzofuranamine

HRID 1928867Notes

Reaction equation

HRID 1928867 reaction equation
[CH2:1]([O:3][C:4]1[C:9]2[C:10](=[N:13]O)[CH2:11][O:12][C:8]=2[CH:7]=[CH:6][CH:5]=1)[CH3:2]>C(O)C.O1CCCC1.[Pd]>[CH2:1]([O:3][C:4]1[C:9]2[CH:10]([NH2:13])[CH2:11][O:12][C:8]=2[CH:7]=[CH:6][CH:5]=1)[CH3:2]

Participants

5

Reactant 1

HCID 866341864-Ethoxy-benzofuran-3-one oxime

Product 1

HCID 686326984-Ethoxy-2,3-dihydro-3-benzofuranamineYield 95.1%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of the above described 4-ethoxy-benzofuran-3-one oxime (4.2 g, 21.7 mmol) in ethanol (200 mL) and tetrahydrofuran (200 mL) with 10% palladium on carbon (4.0 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 the title compound as a light brown solid (3.7 g, 1:1 mixture of product and starting material); MS: m/e=163.3 (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-a34f9ec0ed704df09f9e253877ae25be
Source dataset
uspto-grants-2012_05
Patent number
US08183380B2

Reaction notes

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