Hydrochloric Acid → Methyl 6-chloropyridine-3-carboxylate

HRID 1455079Notes

Reaction equation

HRID 1455079 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][N:3]=1.Cl.[CH3:12]O>>[CH3:12][O:7][C:6](=[O:8])[C:5]1[CH:9]=[CH:10][C:2]([Cl:1])=[N:3][CH:4]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 792226-Chloronicotinic acid

Product 1

HCID 254249Methyl 6-chloropyridine-3-carboxylate

Procedure

6-Chloronicotinic acid (2.0 g) was dissolved in methanol and concentrated hydrochloric acid (3.0 ml) was added. The reaction mixture was refluxed for 5 hours and methanol was removed in vacuum. Ethyl acetate was added and the resulting solution was washed with saturated sodium bicarbonate solution, water and brine. 1H NMR (400 MHz,) δ: 8.92 (d, 1H, J 2.1 Hz), 8.32 (dd, 1H, J 8.4, 2.1 Hz), 7.70 (d, 1H, J 8.4 Hz), 3.90 (s, 3H).

Workup

  1. temperatureThe reaction mixture was refluxed for 5 hours
  2. custommethanol was removed in vacuum
  3. additionEthyl acetate was added
  4. washthe resulting solution was washed with saturated sodium bicarbonate solution, water and brine

Sources & evidence

ORD record
ord-fc4b9de36f194b31924e2447112e8dad
Source dataset
uspto-grants-2009_01
Patent number
US07482340B2

Reaction notes

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