Trimethylsilyldiazomethane → Methyl 2,6-dichloropyridine-3-carboxylate

HRID 1172832Notes

Reaction equation

HRID 1172832 reaction equation
[Cl:1][C:2]1[N:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[CH3:12][Si](C=[N+]=[N-])(C)C>C1C=CC=CC=1.CO>[Cl:1][C:2]1[N:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:3]=1[C:4]([O:6][CH3:12])=[O:5]

Participants

4

Reactant 2

HCID 167693TrimethylsilyldiazomethaneHCID 8540472,6-Dichloronicotinic acid

Product 1

HCID 11106516Methyl 2,6-dichloropyridine-3-carboxylate

Reagents, catalysts & solvents 1

HCID 21927730Benzene methanolSolvent

Procedure

To a solution of 2,6-dichloronicotinic acid (52 g, 0.27 mol) in benzene: MeOH (7:1, 1.0 L) was added dropwise a solution of (trimethylsilyl)diazomethane (1 M in heptane) until gas evolution ceased and the yellow color persisted (ca. 320 mL, 1.2 equiv.). The volatiles were removed and the residue was purified by chromatography on silica gel eluting with 7:1 hexane:ethyl acetate to give the product as a white solid.

Workup

  1. customThe volatiles were removed
  2. customthe residue was purified by chromatography on silica gel eluting with 7:1 hexane

Sources & evidence

ORD record
ord-43782dbdbf4740d9b30fafd196244709
Source dataset
uspto-grants-2010_11
Patent number
US07834036B2

Reaction notes

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