Sodium Hydroxide → (2-Chloropyridin-3-yl)methanol

HRID 1692593Notes

Reaction equation

HRID 1692593 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl:7][C:8]1[N:16]=[CH:15][CH:14]=[CH:13][C:9]=1[C:10](O)=[O:11].[OH-].[Na+]>C1COCC1>[Cl:7][C:8]1[C:9]([CH2:10][OH:11])=[CH:13][CH:14]=[CH:15][N:16]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 762582-Chloronicotinic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 2763647(2-Chloropyridin-3-yl)methanolYield 68.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
50 °C

Procedure

To a suspension of lithium aluminum hydride (8.60 g) in THF (200 mL) was added a solution of 2-chloronicotinic acid (22.4 g) in THF (30 mL) at 0° C., and the mixture was stirred at 50° C. for 1 hr. After the reaction mixture was cooled to 0° C., 1N aqueous sodium hydroxide solution (9 mL) was added. The precipitate was filtered off, and the filtrate was concentrated. The residue was purified by silica gel column chromatography (solvent gradient; 10→25% ethyl acetate/hexane) to give (2-chloropyridin-3-yl)methanol (14.0 g, 68%) as a colorless oil.

Workup

  1. temperatureAfter the reaction mixture was cooled to 0° C.
  2. filtrationThe precipitate was filtered off
  3. concentrationthe filtrate was concentrated
  4. customThe residue was purified by silica gel column chromatography (solvent gradient; 10→25% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-ef0823056ab0476d973e7d0fe7d56e52
Source dataset
uspto-grants-2012_04
Patent number
US08158617B2

Reaction notes

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