7-Methoxyindan-1-one oxime → 7-Methoxy-2,3-dihydro-1H-inden-1-amine

HRID 1695586Notes

Reaction equation

HRID 1695586 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:11]=1[C:10](=[N:12]O)[CH2:9][CH2:8]2.[H][H]>O1CCCC1.CO.[Ni]>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:11]=1[CH:10]([NH2:12])[CH2:9][CH2:8]2

Participants

6

Reactant 2

HCID 5949007-Methoxyindan-1-one oximeHCID 178418361HCID 178418361, compound

Product 1

HCID 186198817-Methoxy-2,3-dihydro-1H-inden-1-amineYield 97%

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 7-methoxy-indan-1-one oxime (CAS 908108-58-7, (E)-oxime 179899-16-2) (22.3 g, 126 mmol)) and Raney-Nickel (11.26 g) in tetrahydrofuran (570 mL) and methanol (570 mL) was hydrogenated at 100 bar hydrogen-pressure at 60° C. for 22 h. Filtered the catalyst off, washed with methanol and tetrahydrofuran, all volatiles were removed in vacuum to give the title compound as a brown oil (19.95 g, 97%, HPLC 0.4 min), MS (ISP) m/e=164.2 [(M+H)+].

Workup

  1. filtrationFiltered the catalyst off,
  2. washwashed with methanol and tetrahydrofuran
  3. customall volatiles were removed in vacuum

Sources & evidence

ORD record
ord-085fab7d1e5a41aaa1d9a12a071251be
Source dataset
uspto-grants-2012_04
Patent number
US08163740B2

Reaction notes

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