Carbon Tetrachloride → Methyl 2-methoxypyridine-3-carboxylate

HRID 580547Notes

Reaction equation

HRID 580547 reaction equation
S(Cl)(Cl)=O.[CH3:5][O:6][C:7]1[C:12]([C:13]([OH:15])=[O:14])=[CH:11][CH:10]=[CH:9][N:8]=1.[C:16](Cl)(Cl)(Cl)Cl>>[CH3:5][O:6][C:7]1[C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:11][CH:10]=[CH:9][N:8]=1

Participants

4

Reactant 3

HCID 5943Carbon TetrachlorideHCID 24386Thionyl ChlorideHCID 7080932-Methoxynicotinic acid

Product 1

HCID 10820973Methyl 2-methoxypyridine-3-carboxylate

Procedure

Thionyl chloride (50 ml.) was added to 2-methoxypyridine-3-carboxylic acid (5 g.) in 50 ml. of carbon tetrachloride and the mixture refluxed for 2 hours. The reaction mixture was cooled, evaporated to solids and chased with multiple portions of fresh carbon tetrachloride. The resulting acid chloride hydrochloride was dissolved in excess methanol (50 ml.), stirred for 16 hours at room temperature, then evaporated an oil and taken up in chloroform. The chloroform solution was washed with two portions of saturated sodium bicarbonate and then one portion of brine, dried over anhydrous magnesium sulfate, filtered and evaporated to yield title product as an oil [4.63 g.; pnmr/CDCl3 /delta (ppm): 3.9 and 4.1 (2s, 6H), 6.9 (m, 1H), 8.2 (m, 2H)].

Workup

  1. temperatureThe reaction mixture was cooled
  2. customevaporated to solids and chased with multiple portions of fresh carbon tetrachloride
  3. dissolutionThe resulting acid chloride hydrochloride was dissolved in excess methanol (50 ml.)
  4. customevaporated an oil
  5. washThe chloroform solution was washed with two portions of saturated sodium bicarbonate
  6. dry with materialone portion of brine, dried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-59ba9ca6171b4e2294f3d9f8e88cfb3e
Source dataset
uspto-grants-1988_06
Patent number
US04753956

Reaction notes

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