6-Butoxy-2,2-dimethylchroman-4-one oxime → 4-Amino-6-butoxy-2,2-dimethylchroman

HRID 618823Notes

Reaction equation

HRID 618823 reaction equation
[CH2:1]([O:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[O:12][C:11]([CH3:17])([CH3:16])[CH2:10][C:9]2=[N:18]O)[CH2:2][CH2:3][CH3:4]>CO.C1COCC1.N.[Ni]>[NH2:18][CH:9]1[C:8]2[C:13](=[CH:14][CH:15]=[C:6]([O:5][CH2:1][CH2:2][CH2:3][CH3:4])[CH:7]=2)[O:12][C:11]([CH3:16])([CH3:17])[CH2:10]1

Participants

6

Reactant 1

HCID 867545196-Butoxy-2,2-dimethylchroman-4-one oxime

Product 1

HCID 218486564-Amino-6-butoxy-2,2-dimethylchromanYield 72.2%

Reagents, catalysts & solvents 4

HCID 935NickelCatalystHCID 222AmmoniaSolventHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 30 g of 6-butoxy-2,2-dimethylchroman-4-one oxime in 500 ml of methanol, 500 ml of THF and 30 ml of ammonia solution was hydrogenated in a shaking duck for 8 h in the presence of Raney nickel. After filtering off the catalyst and concentrating in vacuo, 20.5 g of 4-amino-6-butoxy-2,2-dimethylchroman were obtained.

Workup

  1. filtrationAfter filtering off the catalyst
  2. concentrationconcentrating in vacuo

Sources & evidence

ORD record
ord-8d871723d87446baa2b9ca4469202214
Source dataset
uspto-grants-1999_09
Patent number
US05955607

Reaction notes

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