Methanol → Methyl 5-chloropyridine-3-carboxylate

HRID 877616Notes

Reaction equation

HRID 877616 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].S(=O)(=O)(O)O.[CH3:16]O>>[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([CH:10]=1)[C:7]([O:9][CH3:16])=[O:8]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 2479865-Chloronicotinic acid

Product 1

HCID 15421663Methyl 5-chloropyridine-3-carboxylate

Procedure

5-Chloronicotinic acid (200 mg, 1.269 mmol) was refluxed overnight in the presence of concentrated sulfuric acid (8.20 mg, 0.063 mmol) in methanol (8 mL) at 70° C. The reaction was monitored by TLC. After completion of the reaction, the solvent was removed by vacuum and the compound was purified by column chromatography affording the title compound (120 mg). 1H NMR (400 MHz, CDCl3): δ 9.07 (d, 1H, J=1.6 Hz), 8.72 (d, 1H, J=2.0 Hz), 8.26 (m, 1H), 3.95 (s, 1H).

Workup

  1. customAfter completion of the reaction
  2. customthe solvent was removed by vacuum
  3. customthe compound was purified by column chromatography

Sources & evidence

ORD record
ord-0d82732f7e6441308402226dd4ed784b
Source dataset
uspto-grants-2015_03
Patent number
US08987335B2

Reaction notes

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