Methanol → Methyl 6-chloro-3-methylpyridine-2-carboxylate

HRID 1799554Notes

Reaction equation

HRID 1799554 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([C:8]([OH:10])=[O:9])[C:5]([CH3:11])=[CH:4][CH:3]=1.CO.[Si](C=[N+]=[N-])(C)(C)[CH3:15]>C1COCC1>[Cl:1][C:2]1[N:7]=[C:6]([C:8]([O:10][CH3:15])=[O:9])[C:5]([CH3:11])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 167693TrimethylsilyldiazomethaneHCID 469414706-Chloro-3-methylpyridine-2-carboxylic acid

Product 1

HCID 45489870Methyl 6-chloro-3-methylpyridine-2-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

6-Chloro-3-methylpyridine-2-carboxylic acid (3.69 g, 21.51 mmol) was taken up in THF (100 mL)/MeOH (25 mL). A solution of TMS-diazomethane (21.5 mL, 43.0 mmol) was added and the resulting solution stirred at room temperature for 2 hours. The solvent was removed in vacuo and the residue purified by silica gel chromatography (2-20% EtOAc/hexanes) to give the title compound as a white solid.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue purified by silica gel chromatography (2-20% EtOAc/hexanes)

Sources & evidence

ORD record
ord-67393a263ddc40c8a4f17ce80e687b3f
Source dataset
uspto-grants-2013_01
Patent number
US08344144B2

Reaction notes

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