Ammonia → 4-Amino-6-benzyloxy-2,2-dimethylchroman

HRID 618818Notes

Reaction equation

HRID 618818 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[O:15][C:14]([CH3:20])([CH3:19])[CH2:13][C:12]2=[N:21]O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N>C1COCC1.CO.[Ni]>[NH2:21][CH:12]1[C:11]2[C:16](=[CH:17][CH:18]=[C:9]([O:8][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[CH:10]=2)[O:15][C:14]([CH3:20])([CH3:19])[CH2:13]1

Participants

5

Reactant 2

HCID 222AmmoniaHCID 867545186-Benzyloxy-2,2-dimethylchroman-4-one oxime

Product 1

HCID 212645054-Amino-6-benzyloxy-2,2-dimethylchroman

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

30 g of 6-benzyloxy-2,2-dimethylchroman-4-one oxime were dissolved in 900 ml of THF/methanol (1:1), treated with 25 ml of aqueous ammonia and hydrogenated in a shaking duck using Raney Ni. The catalyst was then filtered off with suction, the filtrate was concentrated in vacuo, the residue was dissolved in EA, dried and concentrated, and the residue was crystallized using petroleum ether, 22.9 g, m.p. 86-88° C.

Workup

  1. filtrationThe catalyst was then filtered off with suction
  2. concentrationthe filtrate was concentrated in vacuo
  3. dissolutionthe residue was dissolved in EA
  4. customdried
  5. concentrationconcentrated
  6. customthe residue was crystallized

Sources & evidence

ORD record
ord-42c78d6848124d6db8a0b782dd2c9e92
Source dataset
uspto-grants-1999_09
Patent number
US05955607

Reaction notes

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