Hydrochloric Acid → Methyl 6-(chloromethyl)pyridine-2-carboxylate

HRID 1871961Notes

Reaction equation

HRID 1871961 reaction equation
O[CH2:2][C:3]1[N:8]=[C:7]([C:9]([O:11][CH3:12])=[O:10])[CH:6]=[CH:5][CH:4]=1.[ClH:13]>C(OCC)(=O)C>[Cl:13][CH2:2][C:3]1[N:8]=[C:7]([C:9]([O:11][CH3:12])=[O:10])[CH:6]=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 11513809Methyl 6-(hydroxymethyl)picolinate

Product 1

HCID 53404482Methyl 6-(chloromethyl)pyridine-2-carboxylate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of the product from step (i) (2.75 g) in ethyl acetate (10 ml) was added 1M ethereal HCl (10 ml). The mixture was stirred for 10 minutes and the precipitate filtered off. This was dissolved in thionyl chloride (20 ml) at 0° C. After 2 hours the mixture was warmed to room temperature. Diethyl ether (100 ml) was added and the precipitate filtered off and used directly in the next step. Yield 1.3 g.

Workup

  1. filtrationthe precipitate filtered off
  2. dissolutionThis was dissolved in thionyl chloride (20 ml) at 0° C
  3. additionDiethyl ether (100 ml) was added
  4. filtrationthe precipitate filtered off

Sources & evidence

ORD record
ord-cdc6d5c7a26e4a64b9d3578f6b9f0d34
Source dataset
uspto-grants-2000_08
Patent number
US06107297

Reaction notes

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