Ammonium formate → 2,2-Dimethyl-1,3-dioxan-5-amine

HRID 1111256Notes

Reaction equation

HRID 1111256 reaction equation
[CH3:1][C:2]1([CH3:11])[O:7][CH2:6][CH:5]([N+:8]([O-])=O)[CH2:4][O:3]1.C([O-])=O.[NH4+]>CO.[Pd]>[CH3:1][C:2]1([CH3:11])[O:7][CH2:6][CH:5]([NH2:8])[CH2:4][O:3]1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 108774282,2-Dimethyl-5-nitro-1,3-dioxane

Product 1

HCID 117686082,2-Dimethyl-1,3-dioxan-5-amineYield 70.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

220 mg 5% Pd/C was added to a solution of 500 mg 2,2-dimethyl-5-nitro-1,3-dioxane (3.1 mmoles) in 30 ml methanol. Ammonium formate (985 mg, 15.6 mmoles) was then added, and the mixture was refluxed for three hours. The reaction solution was then filtered, and the filtrate concentrated in vacuo to yield 286 mg 2,2-dimethyl-5-amino-1,3-dioxane (70% yield).

Workup

  1. temperaturethe mixture was refluxed for three hours
  2. filtrationThe reaction solution was then filtered
  3. concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record
ord-42e6471954b34b13ba19fe924c582782
Source dataset
uspto-grants-1990_12
Patent number
US04978793

Reaction notes

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