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

HRID 567056Notes

Reaction equation

HRID 567056 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 with Raney Ni. The catalyst was then filtered off with suction, the filtrate was concentrated in vac., the residue was dissolved in EA, the solution was 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 vac
  3. dissolution, the residue was dissolved in EA
  4. customthe solution was dried
  5. concentrationconcentrated
  6. customthe residue was crystallized

Sources & evidence

ORD record
ord-0557b19c37264c7094d4ce69a43564fa
Source dataset
uspto-grants-2001_01
Patent number
US06177449B1

Reaction notes

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