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

HRID 595231Notes

Reaction equation

HRID 595231 reaction equation
B.C1COCC1.[O:7]=[C:8]1[CH:13]=[C:12]([C:14](O)=[O:15])[CH:11]=[CH:10][NH:9]1.CO>C1COCC1>[OH:15][CH2:14][C:12]1[CH:11]=[CH:10][NH:9][C:8](=[O:7])[CH:13]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 2807562-Hydroxyisonicotinic AcidHCID 2723981Borane;tetrahydrofuran

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

Borane-THF (29 mL, 1.0 M) was added to a solution of 2-oxo-1,2-dihydropyridine-4-carboxylic acid (1 g, 7.19 mmol) in THF (15 mL) at 0° C. The mixture was stirred at 25° C. for 2 hours. Methanol was added and the mixture was concentrated under reduced pressure to afford 4-(hydroxymethyl)pyridin-2(1H)-one. MS ESI calc'd. for C6H8NO2 [M+H]+ 126. found 126. 1H NMR (400 MHz, CD3OD) δ 7.40 (d, J=6.8 Hz, 1H), 6.58 (s, 1H), 6.38 (d, J=6.4 Hz, 1H), 4.52 (s, 2H).

Workup

  1. concentrationthe mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-ad92fbbd6b844b6983e78378390614f6
Source dataset
uspto-grants-2016_01
Patent number
US09242984B2

Reaction notes

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