Methyl chloroformate → Methyl 6-chloropyridine-3-carboxylate

HRID 1292144Notes

Reaction equation

HRID 1292144 reaction equation
[CH2:1](N(CC)CC)C.[Cl:8][C:9]1[CH:17]=[CH:16][C:12]([C:13]([OH:15])=[O:14])=[CH:11][N:10]=1.ClC(OC)=O>ClCCl>[Cl:8][C:9]1[CH:17]=[CH:16][C:12]([C:13]([O:15][CH3:1])=[O:14])=[CH:11][N:10]=1

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 8471TriethylamineHCID 792226-Chloronicotinic acid

Product 1

HCID 254249Methyl 6-chloropyridine-3-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triethylamine (28.4 g) was added to a solution of 6-chloronicotinic acid (40 g) in dry dichloromethane (900 ml). The mixture was cooled in an ice bath and methyl chloroformate (26.8 g) was added dropwise. The mixture was stirred at room temperature overnight, washed in turn with water, aqueous sodium hydrogen carbonate and brine. The organic phase was dried over magnesium sulfate, filtered and evaporated to give methyl 6-chloronicotinate.

Workup

  1. temperatureThe mixture was cooled in an ice bath
  2. washwashed in turn with water, aqueous sodium hydrogen carbonate and brine
  3. dry with materialThe organic phase was dried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-a1c87dd0cdc24aa8988bbffd3d3fc41f
Source dataset
uspto-grants-1998_05
Patent number
US05756524

Reaction notes

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