Triethylamine → Methyl 6-chloropyridine-3-carboxylate

HRID 249482Notes

Reaction equation

HRID 249482 reaction equation
O[C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][N:3]=1.C(N(CC)CC)C.P(Cl)(Cl)([Cl:21])=O>C(#N)C>[Cl:21][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 24813Phosphorus oxychlorideHCID 178498304HCID 178498304, compound

Product 1

HCID 254249Methyl 6-chloropyridine-3-carboxylate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

In 100 ml of acetonitrile was dissolved 4.0 g (0.026 mole) of methyl 6-hydroxynicotinate followed by addition of 0.9 ml of triethylamine. The mixture was refluxed and 3.7 ml of phosphorus oxychloride was added dropwise with stirring over a period of 15 minutes. The mixture was further refluxed for 3 hours. After cooling, the acetonitrile was distilled off and the residue was diluted with 20 ml of water and adjusted to pH about 8 with a saturated aqueous solution of sodium hydrogen carbonate. The resulting crystals are collected by filtration, rinsed with water and dried to give 3.6 g of methyl 6-chloronicotinate as pale yellow needles.

Workup

  1. temperatureThe mixture was refluxed
  2. temperatureThe mixture was further refluxed for 3 hours
  3. temperatureAfter cooling
  4. distillationthe acetonitrile was distilled off
  5. additionthe residue was diluted with 20 ml of water
  6. filtrationThe resulting crystals are collected by filtration
  7. washrinsed with water
  8. customdried

Sources & evidence

ORD record
ord-ea6f6b006e9e46feb67ccdcfb0120f4b
Source dataset
uspto-grants-1993_05
Patent number
US05214152

Reaction notes

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