Hydrochloric Acid → Methyl 2-(chloromethyl)-4-pyridinecarboxylate

HRID 1196510Notes

Reaction equation

HRID 1196510 reaction equation
O[CH2:2][C:3]1[CH:8]=[C:7]([C:9]([O:11][CH3:12])=[O:10])[CH:6]=[CH:5][N:4]=1.[ClH:13]>COC(=O)C>[Cl:13][CH2:2][C:3]1[CH:8]=[C:7]([C:9]([O:11][CH3:12])=[O:10])[CH:6]=[CH:5][N:4]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 13276248Methyl 2-(hydroxymethyl)pyridine-4-carboxylate

Product 1

HCID 14625089Methyl 2-(chloromethyl)-4-pyridinecarboxylate

Reagents, catalysts & solvents 1

HCID 6584Methyl AcetateSolvent

Procedure

A solution of the product of stage (ii) in methylacetate (5 ml) was treated with ethereal hydrogen chloride (5 ml). The resulting solid was collected by filtration and added to thionyl chloride (7.5 ml) at 0°-5°. The mixture was stirred at 0°-5° for 3 h and then at ambient temperature for 1 h. Diethyl ether (100 ml) was added and the resulting solid was collected by filtration and washed with diethylether (2×50 ml), to give the title compound as a solid (1.7 g) T.l.c. Silica dichloromethane/methanol/ammonia 75:10:2 Rf 0.8.

Workup

  1. filtrationThe resulting solid was collected by filtration
  2. additionadded to thionyl chloride (7.5 ml) at 0°-5°
  3. waitat ambient temperature for 1 h
  4. additionDiethyl ether (100 ml) was added
  5. filtrationthe resulting solid was collected by filtration
  6. washwashed with diethylether (2×50 ml)

Sources & evidence

ORD record
ord-f5b83c88dd044360bd4cb79d414dd4b2
Source dataset
uspto-grants-1992_05
Patent number
US05114945

Reaction notes

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