Methanol → Methyl 2-chloronicotinate

HRID 1251912Notes

Reaction equation

HRID 1251912 reaction equation
S(Cl)(Cl)=O.Cl.[Cl:6][C:7]1[C:12]([C:13]([OH:15])=[O:14])=[CH:11][CH:10]=[CH:9][N:8]=1.[CH3:16]O>>[Cl:6][C:7]1[C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:11][CH:10]=[CH:9][N:8]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 27628002-Chloropyridine-3-carboxylic acid--hydrogen chloride (1/1)

Product 1

HCID 819931Methyl 2-chloronicotinate

Procedure

Thionyl chloride (3.8 g.) was added dropwise, over 10 minutes, to a solution of 2-chloropyridin-3-carboxylic acid HCl salt (1.0 g.) in methanol, stirred under an inert atmosphere and cooled in an ice/salt bath. The reaction was stirred for a further 5 days at ambient temperature. The methanol was evaporated away and the residue treated with saturated sodium bicarbonate solution and extracted with ethyl acetate. The extracts were dried and evaporated to dryness to give methyl 2-chloropyridin-3-carboxylate as a colourless liquid (0.9 g.)

Workup

  1. temperaturecooled in an ice/salt bath
  2. stirringThe reaction was stirred for a further 5 days at ambient temperature
  3. customThe methanol was evaporated away
  4. additionthe residue treated with saturated sodium bicarbonate solution
  5. extractionextracted with ethyl acetate
  6. customThe extracts were dried
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-9eadd93bdfe340d6a42b5f09372ccb4c
Source dataset
uspto-grants-2002_01
Patent number
US06342765B1

Reaction notes

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