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

HRID 1594194Notes

Reaction equation

HRID 1594194 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 (ESI), (M+H)+153.4; 1H NMR (CDCl3) δ8.06 (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-0f15458e3d2e48e9ad5dc4e82fd3dbda
Source dataset
uspto-grants-2007_11
Patent number
US07300936B2

Reaction notes

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