2-Chloro-6-methylpyridine-4-carboxylic acid → (2-Chloro-6-methylpyridin-4-yl)methanol

HRID 1814015Notes

Reaction equation

HRID 1814015 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([CH3:11])[N:10]=1)[C:5](O)=[O:6].B.C1COCC1>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:5][OH:6])[CH:8]=[C:9]([CH3:11])[N:10]=1

Participants

4

Reactant 2

HCID 1412092-Chloro-6-methylpyridine-4-carboxylic acidHCID 2723981Borane;tetrahydrofuran

Product 1

HCID 22504306(2-Chloro-6-methylpyridin-4-yl)methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

2-Chloro-6-methyl-isonicotinic acid (13-1, 2.00 g, 11.7 mmol) was dissolved in 10 mL of anhydrous THF under N2. The solution was cooled to 0° C., and borane-THF (1 M solution in THF, 14.0 mL, 14.0 mmol) was added slowly. The reaction was heated to reflux. After 3 hours the reaction was cooled to room temperature and quenched slowly with 1M HCl (aq) until cessation of bubbling. The pH of the solution was adjusted to 7 with saturated NaHCO3 (aq). The mixture was extracted 3× with EtOAc and the extracts dried over Na2SO4, filtered and concentrated to afford (2-chloro-6-methyl-pyridin-4-yl)-methanol. 1H NMR (CDCl3) δ 7.16 (s, 1H), 7.06 (s, 1H), 4.70 (d, 2H, J=5.8 Hz), 2.53 (s, 3H), 1.95 (t, 1H, J=5.8 hz).

Workup

  1. temperatureThe reaction was heated to reflux
  2. temperatureAfter 3 hours the reaction was cooled to room temperature
  3. customquenched slowly with 1M HCl (aq) until cessation
  4. customof bubbling
  5. extractionThe mixture was extracted 3× with EtOAc
  6. dry with materialthe extracts dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-ba1ff8a0affa4d28bb9e8115c714afeb
Source dataset
uspto-grants-2005_04
Patent number
US06875767B2

Reaction notes

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