6-Bromopyridine-2-carboxylic acid → Ethyl 6-Bromopicolinate

HRID 2264789Notes

Reaction equation

HRID 2264789 reaction equation
[Br:1][C:2]1[N:7]=[C:6]([C:8]([OH:10])=[O:9])[CH:5]=[CH:4][CH:3]=1.Cl.[CH2:12](O)[CH3:13]>>[Br:1][C:2]1[N:7]=[C:6]([C:8]([O:10][CH2:12][CH3:13])=[O:9])[CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 5939196-Bromopyridine-2-carboxylic acidHCID 21887872Ethanol hydrochloride

Product 1

HCID 2758810Ethyl 6-BromopicolinateYield 92%

Procedure

6-Bromo-2-pyridinecarboxylic acid (925 mg, 4.95 mmol) (Aldrich) was dissolved in hydrochloric acid/ethanol (1.25 M, 20 ml) and stirred under reflux for 3 h. Then the solvent was evaporated under reduced pressure. The remaining residue was taken up with DCM and washed with saturated aqueous NaHCO3 solution. Evaporation of the solvent afforded the title compound (1.045 g, 92%). The material was used in the following step without any further purification; 1H-NMR (300 MHz, CDCl3) δ (ppm): 8.1-8.0 (m, 1H), 7.8-7.5 (m, 2H), 4.4 (q, 2H), 1.4 (t, 3H).

Workup

  1. temperatureunder reflux for 3 h
  2. customThen the solvent was evaporated under reduced pressure
  3. washwashed with saturated aqueous NaHCO3 solution
  4. customEvaporation of the solvent

Sources & evidence

ORD record
ord-5f9b6f1d6a3b4daead4151b63f77d464
Source dataset
uspto-grants-2010_12
Patent number
US07855218B2

Reaction notes

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