Water → HCID 71108574, compound

HRID 64447Notes

Reaction equation

HRID 64447 reaction equation
[CH3:1][C:2]1([CH3:18])[O:7][CH2:6][C:5]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([CH3:17])[CH:12]=2)([N+:8]([O-])=O)[CH2:4][O:3]1.O>C(O)C.[Ni]>[CH3:1][C:2]1([CH3:18])[O:3][CH2:4][C:5]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([CH3:17])[CH:12]=2)([NH2:8])[CH2:6][O:7]1

Participants

5

Reactant 2

HCID 962WaterHCID 86713462HCID 86713462, compound

Product 1

HCID 71108574HCID 71108574, compoundYield 110%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent3×

Procedure

To a mixture of 1.6 g of 2,2-dimethyl-5-(3-methylphenyl)-5-nitro-1,3-dioxane in 24 ml of ethanol was added a suspension of a Raney nickel (manufactured by Aldrich, product obtained by washing 1 ml of an aqueous suspension with water and ethanol) in 9 ml of ethanol, followed by stirring for 22 hours under a hydrogen atmosphere at 4 atm. The reaction mixture was filtered over Celite and the solvent was then evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain 1.55 g of 2,2-dimethyl-5-(3-methylphenyl)-1,3-dioxan-5-amine.

Workup

  1. additionwas added
  2. filtrationThe reaction mixture was filtered over Celite
  3. customthe solvent was then evaporated under reduced pressure
  4. customThe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-4cb9b4f738374774b71c07fdb7e68c40
Source dataset
uspto-grants-2016_09
Patent number
US09447090B2

Reaction notes

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