Methanol → 4-(Hydroxymethyl)pyridin-2(1H)-one

HRID 1475233Notes

Reaction equation

HRID 1475233 reaction equation
[O:1]=[C:2]1[CH:7]=[C:6]([C:8](OC)=[O:9])[CH:5]=[CH:4][NH:3]1.[H-].C([Al+]CC(C)C)C(C)C.CO.O>C1COCC1>[OH:9][CH2:8][C:6]1[CH:5]=[CH:4][NH:3][C:2](=[O:1])[CH:7]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 280755Methyl 2-oxo-1,2-dihydropyridine-4-carboxylateHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 110946104-(Hydroxymethyl)pyridin-2(1H)-oneYield 61.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of methyl 2-oxo-1,2-dihydropyridine-4-carboxylate (300 mg, 1.96 mmol) in THF (20 mL) was added diisobutylaluminium hydride (1.0 M in THF, 20 mL, 20 mmol). The mixture was stirred at RT for 3 h, then MeOH (2 mL) and H2O (1 mL) were added. The mixture was stirred at RT for 20 minutes and concentrated under reduced pressure. The crude product was purified by silica gel chromatography (DCM:MeOH=8:1) to afford 4-(hydroxymethyl)pyridin-2(1H)-one as a white solid (150 mg, 61.2%). MS (ES+) C6H7NO2 requires: 125. found: 126 [M+H]+.

Workup

  1. stirringThe mixture was stirred at RT for 20 minutes
  2. concentrationconcentrated under reduced pressure
  3. customThe crude product was purified by silica gel chromatography (DCM:MeOH=8:1)

Sources & evidence

ORD record
ord-b06f4a02a1114cfdb2ed6cb8ab94b19a
Source dataset
uspto-grants-2015_04
Patent number
US09018380B2

Reaction notes

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