Ammonium Hydroxide → 3-(BENZYLOXY)-2-METHYL-4(1H)-PYRIDINONE

HRID 913028Notes

Reaction equation

HRID 913028 reaction equation
[CH2:1]([O:8][C:9]1[C:14](=[O:15])[CH:13]=[CH:12]O[C:10]=1[CH3:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[NH4+:18]>C(O)C>[CH2:1]([O:8][C:9]1[C:14](=[O:15])[CH:13]=[CH:12][NH:18][C:10]=1[CH3:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 14923Ammonium Hydroxide2×HCID 14901193-Benzyloxy-2-methyl-4-pyrone

Product 1

HCID 27264163-(BENZYLOXY)-2-METHYL-4(1H)-PYRIDINONEYield 64%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A clear solution of 3-(benzyloxy)-2-methyl-4H-pyran-4-one (150 g, 0.69 mol), ethanol (300 mL) and ammonium hydroxide (28.0-30.0% solution, 690 mL, 10.5 mol) in a 2 L 3-necked round bottom flask equipped with a mechanical stirrer was heated to reflux for 5 h. The reaction mixture was allowed to cool to room temperature, and a further 230 mL of ammonium hydroxide (3.5 mol) was added. The resulting solution was heated to reflux for another 3.5 h, then allowed to cool to RT and stirred for overnight. A solid product had separated, and was collected by suction filtration. Thus, 95 g of 3-benzyloxy-2-methyl-1H-pyridin-4-one (64% yield) was obtained as a first crop. HPLC Method 4 (Example 24), RT=10.7 min, HPLC purity (peak percent area): 99% at λ=280 nm)). 1H NMR (DMSO-d6) δ ppm: 11.3 (br s, 1H), 7.46 (s, 1H), 7.35, (m, 5H), 6.13 (s, 1H), 5.04 (s, 2H), 2.05 (s, 3H); 1H NMR (DMSO-d6+D2O) δ ppm: 7.47 (d, J=7.0 Hz, 1H), 7.39, (m, 5H), 6.20 (d, J=7.0 Hz, 1H), 5.01 (s, 2H), 2.03 (s, 3H).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 5 h
  3. temperatureThe resulting solution was heated
  4. temperatureto reflux for another 3.5 h
  5. temperatureto cool to RT
  6. customA solid product had separated
  7. filtrationwas collected by suction filtration

Sources & evidence

ORD record
ord-a11d18c20ac54e439d7ae1f5df5d220e
Source dataset
uspto-grants-2011_09
Patent number
US08026261B2

Reaction notes

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