Methanol → Methyl 2-chloronicotinate

HRID 964031Notes

Reaction equation

HRID 964031 reaction equation
[Cl:1][C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].S(Cl)(Cl)=O.[CH3:15]O>>[CH3:15][O:5][C:4](=[O:6])[C:3]1[CH:7]=[CH:8][CH:9]=[N:10][C:2]=1[Cl:1]

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 762582-Chloronicotinic acid

Product 1

HCID 819931Methyl 2-chloronicotinateYield 89%

Procedure

To a suspension of 2-chloronicotinic acid 3 (15.8 g, 0.1 mol) in 100 ml of dry MeOH at 0° C. was added thionyl chloride (17.8 g, 0.15 mol) dropwise. The reaction was then slowly warmed to room temperature and stirred for 2 days. The solvent was then removed via vacuum and the residue was dissolved in sat. NaHCO3. The resulted basic solution was then extracted with EtOAc (3×100 ml). The combined organic phases were washed with brine, dried with NaSO4, concentrated via vacuum to give 2-chloronicotinic methyl ester 4(15.3 g, 89%) as an oil: 1H NMR (CDCl3, 300 MHZ) δ 8.52 (dd, J=1.8, 4.5 Hz, 1H), δ 8.19 (dd, J=2.1, 7.8 Hz, 1H), δ 7.38 (dd, J=4.8, 7.8 Hz, 1H), δ 3.97 (s, 3H)

Workup

  1. customThe solvent was then removed via vacuum
  2. dissolutionthe residue was dissolved in sat. NaHCO3
  3. extractionThe resulted basic solution was then extracted with EtOAc (3×100 ml)
  4. washThe combined organic phases were washed with brine
  5. dry with materialdried with NaSO4
  6. concentrationconcentrated via vacuum

Sources & evidence

ORD record
ord-b905f4375cf942319d819f20983acce9
Source dataset
uspto-grants-1998_06
Patent number
US05767134

Reaction notes

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