Aluminium lithium hydride → [6-(Dimethylamino)pyridin-3-yl]methanol

HRID 507294Notes

Reaction equation

HRID 507294 reaction equation
[CH3:1][N:2]([CH3:13])[C:3]1[CH:12]=[CH:11][C:6]([C:7](OC)=[O:8])=[CH:5][N:4]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>CCOCC>[CH3:1][N:2]([CH3:13])[C:3]1[CH:12]=[CH:11][C:6]([CH2:7][OH:8])=[CH:5][N:4]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 23271116Methyl 6-(dimethylamino)pyridine-3-carboxylate

Product 1

HCID 12259943[6-(Dimethylamino)pyridin-3-yl]methanol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of methyl 6-dimethylamino-nicotinate (4.14 g, 23.0 mmol) in anhydrous ether (80 mL) at 0° C. was treated with lithium aluminum hydride (1 M in ether, 20 mL, 20 mmol). The mixture was stirred at rt for 0.5 h, cooled again to 0° C. and quenched slowly with sat. aq. NaHCO3 (10 mL). The resulting mixture was stirred at rt for 0.5 h, filtered, and washed with ether. The combined filtrates were dried over Na2SO4 and concentrated to give the title compound as a beige waxy solid (3.5 g, 100%). MS (EST), (M+H)+ 153.4; 1H NMR (CDCl3) δ 8.06 (d, 1H, J=2.4), 7.47 (dd, 1H, J=2.4, 8.8), 6.45 (d, 1H, J=8.8), 4.50 (s, 2H), 3.06 (s, 6H), 1.98 (br s, 1H).

Workup

  1. temperaturecooled again to 0° C.
  2. customquenched slowly with sat. aq. NaHCO3 (10 mL)
  3. stirringThe resulting mixture was stirred at rt for 0.5 h
  4. filtrationfiltered
  5. washwashed with ether
  6. dry with materialThe combined filtrates were dried over Na2SO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-1c22458936d04fa4b8f07f6d3dd1d6f2
Source dataset
uspto-grants-2010_08
Patent number
US07786122B2

Reaction notes

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