Ethyl 2-chloroisonicotinate → (2-Chloropyridin-4-yl)methanol

HRID 899981Notes

Reaction equation

HRID 899981 reaction equation
[BH4-].[Na+].[Cl:3][C:4]1[CH:9]=[C:8]([C:10](OCC)=[O:11])[CH:7]=[CH:6][N:5]=1>C(O)C.ClCCl>[Cl:3][C:4]1[CH:9]=[C:8]([CH2:10][OH:11])[CH:7]=[CH:6][N:5]=1

Participants

5

Reactant 2

HCID 2762942Ethyl 2-chloroisonicotinateHCID 4311764Sodium borohydride

Product 1

HCID 7062237(2-Chloropyridin-4-yl)methanolYield 76%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

2.04 g of sodium borohydride are added portionwise to a solution of 1.7 g of ethyl 2-chloropyridine-4-carboxylate in 20 ml of ethanol, under an inert atmosphere of argon at a temperature in the region of 0° C. The reaction mixture is refluxed with stirring for 3 hours and then concentrated to dryness under reduced pressure. The residue thus obtained is taken up in dichloromethane and then washed with water. The organic phase is dried over magnesium sulfate, filtered and then concentrated to dryness under reduced pressure. 1 g of 2-chloro-4-(hydroxymethyl)pyridine is thus obtained.

Workup

  1. temperatureThe reaction mixture is refluxed
  2. concentrationconcentrated to dryness under reduced pressure
  3. customThe residue thus obtained
  4. washwashed with water
  5. dry with materialThe organic phase is dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-801a40bbdf4c4f479a3e84489fb77a03
Source dataset
uspto-grants-2008_04
Patent number
US07354933B2

Reaction notes

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