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

HRID 2289618Notes

Reaction equation

HRID 2289618 reaction equation
C[O:2][C:3]([C:5]1[CH:10]=[CH:9][NH:8][C:7](=[O:11])[CH:6]=1)=O.CN(C=O)C.[Li+].[BH4-].CO>C1COCC1.CO.C(Cl)(Cl)Cl.O>[OH:2][CH2:3][C:5]1[CH:10]=[CH:9][NH:8][C:7](=[O:11])[CH:6]=1

Participants

8

Reactant 4

HCID 887MethanolHCID 6228DimethylformamideHCID 280755Methyl 2-oxo-1,2-dihydropyridine-4-carboxylateHCID 4148881Lithium borohydride

Product 1

HCID 110946104-(Hydroxymethyl)pyridin-2(1H)-one

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 21584188Chloroform methanolSolvent2×

Procedure

2-Oxo-1,2-dihydropyridine-4-carboxylic acid methyl ester (1.8 g, 12.2 mmol), prepared as described in J. Org. Chem., 26, 428 (1961), was suspended in THF(100 ml). A small amount of DMF was added to help increase solubility. LiBH4 (61 mmol) was added and the reaction was stirred for 18 hours at room temperature. MeOH and H2O are added to quench the reaction. The reaction is then concentrated to yield a yellow oil. Flash chromatography (5% MeOH/CHCl3 to 20% MeOH/CHCl3) yielded 4-hydroxymethyl-1H-pyridin-2-one as a white solid.

Workup

  1. temperatureto help increase solubility
  2. customto quench
  3. customthe reaction
  4. concentrationThe reaction is then concentrated
  5. customto yield a yellow oil

Sources & evidence

ORD record
ord-24944cd9dfbb4e2a8c8636f53f6911d9
Source dataset
uspto-grants-2000_07
Patent number
US06093737

Reaction notes

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