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

HRID 1187494Notes

Reaction equation

HRID 1187494 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-8553249172c44e0087d4bd969c3b349f
Source dataset
uspto-grants-2014_03
Patent number
US08673943B2

Reaction notes

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