Acetic Acid → 6-(Hydroxymethyl)pyridin-2-ol

HRID 1373149Notes

Reaction equation

HRID 1373149 reaction equation
[NH:1]1[C:6]([C:7](O)=[O:8])=[CH:5][CH:4]=[CH:3][C:2]1=[O:10].COCCOC.[H-].[Al+3].[Li+].[H-].[H-].[H-].C(O)(=O)C>C1COCC1>[OH:8][CH2:7][C:6]1[NH:1][C:2](=[O:10])[CH:3]=[CH:4][CH:5]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 80711,2-DimethoxyethaneHCID 2427216-Hydroxypicolinic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 224765516-(Hydroxymethyl)pyridin-2-olYield 32%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

1H-Pyridin-2-one-6-carboxylic acid (2.51 g, 18 mmol) was suspended in dry THF (30 ml) and 1,2-dimethoxyethane (10 ml) under argon. Lithium aluminium hydride (1.0 M in diethyl ether) (30 ml, 30 mmol) was added and the mixture heated to reflux. After 67 h heating was stopped, the mixture cooled to 0° C. and acetic acid (7 ml) added. The solvent was removed in vacuo and the residue purified by flash column chromatography on silica gel, eluting with 20–30% methanol in dichloromethane, to give the title compound as tan needles (0.714 g, 32%); δH (400 MHz; CD3OD) 4.47 (2H, s), 6.38 (1H, d, J 6.8), 6.41 (1H, d, J 9.2), 7.56 (1H, dd, J 6.8, 9.2); m/z (ES+) 126 (100%, [MH]+).

Workup

  1. temperaturethe mixture heated to reflux
  2. temperatureAfter 67 h heating
  3. customThe solvent was removed in vacuo
  4. customthe residue purified by flash column chromatography on silica gel
  5. washeluting with 20–30% methanol in dichloromethane

Sources & evidence

ORD record
ord-c600c20c83374688a148dffa194c4eab
Source dataset
uspto-grants-2007_01
Patent number
US07160907B2

Reaction notes

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