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

HRID 1928857Notes

Reaction equation

HRID 1928857 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>C(O)C.[Pd]>[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

4

Reactant 1

HCID 5949007-Methoxyindan-1-one oxime

Product 1

HCID 186198817-Methoxy-2,3-dihydro-1H-inden-1-amineYield 64%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 7-methoxy-indan-1-one oxime (CAS no: 908108-58-7, (E)-oxime 179899-16-2) (4.59 g, 25.9 mmol) in ethanol (500 mL) with 10% palladium on carbon (4.59 g) was hydrogenated at 23° C. and atmospheric pressure for 16 h. Filtered the catalyst off, washed with ethanol, evaporated the filtrate totally and dried in high vacuum to give the title compound as a brown oil (2.7 g, 64%); MS: m/e=164.2 (M+H+).

Workup

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

Sources & evidence

ORD record
ord-f0aed533cb53483dbc3ef91262a65b11
Source dataset
uspto-grants-2012_05
Patent number
US08183380B2

Reaction notes

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