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

HRID 630001Notes

Reaction equation

HRID 630001 reaction equation
[Cl:1][C:2]1[C:7]([CH:8]=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[BH4-].[Na+].[Cl-].[NH4+]>CO>[Cl:1][C:2]1[C:7]([CH2:8][OH:9])=[CH:6][CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 7376072-Chloro-3-pyridinecarboxaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 2763647(2-Chloropyridin-3-yl)methanolYield 40%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a 0° C. solution of 2-chloropyridine-3-carbaldehyde (2.0 g, 14.1 mmol) in anhydrous methanol (80 mL) was added sodium borohydride (550 mg, 14.5 mmol). The reaction mixture was stirred at room temperature for 3 hours. Saturated ammonium chloride solution (20 mL) was added. The resultant mixture was extracted with dichloromethane (3×20 mL). The organic extracts were combined, dried over MgSO4, filtered, evaporated, and dried in vacuo, affording (2-chloropyridin-3-yl)methanol (800 mg, 40% yield). The product was used without further purification.

Workup

  1. extractionThe resultant mixture was extracted with dichloromethane (3×20 mL)
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. customevaporated
  5. customdried in vacuo

Sources & evidence

ORD record
ord-b378458a02ab42539518cf680662ab8b
Source dataset
uspto-grants-2016_04
Patent number
US09315521B2

Reaction notes

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