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

HRID 1819389Notes

Reaction equation

HRID 1819389 reaction equation
[Cl:1][C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4](O)=[O:5].S(Cl)(Cl)=O.[BH4-].[Na+].[Na+].[Cl-]>O>[Cl:1][C:2]1[C:3]([CH2:4][OH:5])=[CH:7][CH:8]=[CH:9][N:10]=1

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 24386Thionyl ChlorideHCID 762582-Chloronicotinic acidHCID 4311764Sodium borohydride2×

Product 1

HCID 2763647(2-Chloropyridin-3-yl)methanolYield 90.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2-chloronicotinic acid (5.0 g, 31.7 mmol) and thionyl chloride (20 mL) was heated at reflux for 1.5 h. The reaction mixture was concentrated in vacuo to remove an excess thionyl chloride. The resulting solid was added in portions to a solution of sodium borohydride (4.3 g, 114 mmol) in water at 10° C. The reaction was maintained at 10-15° C. during the addition to NaBH4. The reaction mixture was then warmed to room temperature. The mixture was saturated with NaCl and extracted with ether (30 mL×3). The combined organic layer was dried over MgSO4 and concentrated in vacuo to afford 4.1 g (90%) of (2-chloro-pyridin-3-yl)-methanol.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 1.5 h
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. customto remove an excess thionyl chloride
  5. extractionextracted with ether (30 mL×3)
  6. dry with materialThe combined organic layer was dried over MgSO4
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9bba2770f34b4cbfbb2eb2805cb2c4c3
Source dataset
uspto-grants-2009_10
Patent number
US07601714B2

Reaction notes

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