Ammonia → 5-amino-2,2-dimethyl-2H-pyran-3(6H)-one

HRID 478295Notes

Reaction equation

HRID 478295 reaction equation
[CH3:1][C:2]1([CH3:10])[C:7](=[O:8])[CH2:6][C:5](=O)[CH2:4][O:3]1.S(=O)(=O)(O)O.[NH3:16]>C(O)C>[NH2:16][C:5]1[CH2:4][O:3][C:2]([CH3:10])([CH3:1])[C:7](=[O:8])[CH:6]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 1118Sulfuric AcidHCID 140728872,2-dimethyl-2H-pyran-3,5(4H,6H)-dione

Product 1

HCID 180009685-amino-2,2-dimethyl-2H-pyran-3(6H)-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

The product from Example 66C (1.5 g, 11 mmol) in ethanol (40 mL) was treated with concentrated sulfuric acid (0.4 mL), refluxed for 4 hours, cooled to ambient temperature, treated with 2M ammonia in ethanol (50 mL), stirred at ambient temperature for 16 hours and concentrated. The residue was purified by chromatography on silica gel eluting with 10% methanol in dichloromethane to provide the title compound (1.0 g).

Workup

  1. temperaturerefluxed for 4 hours
  2. concentrationconcentrated
  3. customThe residue was purified by chromatography on silica gel eluting with 10% methanol in dichloromethane

Sources & evidence

ORD record
ord-2ea5371c5e80499090bfc097ba137d65
Source dataset
uspto-grants-2003_11
Patent number
US06642222B2

Reaction notes

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