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

HRID 1695582Notes

Reaction equation

HRID 1695582 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.[H][H]>O1CCCC1.CO.[Ni]>[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

6

Reactant 2

HCID 866341844-Methoxy-benzofuran-3-one oximeHCID 178418361HCID 178418361, compound

Product 1

HCID 672125224-Methoxy-2,3-dihydrobenzofuran-3-amineYield 98%

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of the above described 4-methoxy-benzofuran-3-one oxime (27.7 g, 155 mmol; HPLC 1.448 min) and Raney-Nickel (13.85 g) in tetrahydrofuran (700 mL) and methanol (700 mL) was hydrogenated at 100 bar hydrogen-pressure at 100° C. for 22 h. Filtered the catalyst off, washed with methanol and tetrahydrofuran, all volatiles very removed in vacuum to give the title compound as a brown oil (24.7 g, 98%, HPLC 0.4 min), MS (ISP) m/e=166.2 [(M+H)+].

Workup

  1. additionA mixture of the
  2. filtrationFiltered the catalyst off,
  3. washwashed with methanol and tetrahydrofuran
  4. customall volatiles very removed in vacuum

Sources & evidence

ORD record
ord-bb91425f258046d6abd6dc73002dcc6a
Source dataset
uspto-grants-2012_04
Patent number
US08163740B2

Reaction notes

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