Oxalyl chloride → Methyl 2-(chlorocarbonyl)pyridine-4-carboxylate

HRID 2404288Notes

Reaction equation

HRID 2404288 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][N:8]=[C:7]([C:11]([OH:13])=O)[CH:6]=1)=[O:4].C(Cl)(=O)C([Cl:17])=O>ClCCl>[Cl:17][C:11]([C:7]1[CH:6]=[C:5]([CH:10]=[CH:9][N:8]=1)[C:3]([O:2][CH3:1])=[O:4])=[O:13]

Participants

4

Reactant 2

HCID 65578Oxalyl chlorideHCID 133537524-(Methoxycarbonyl)pyridine-2-carboxylic acid

Product 1

HCID 45081772Methyl 2-(chlorocarbonyl)pyridine-4-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 4-(methoxycarbonyl)picolinic acid (150 g, 1.62 mol) in dichloromethane (500 mL) was added oxalyl chloride (400 mL) keeping the temperature at 25-30° C. for 3 days. The reaction was evaporated in vacuo to afford methyl 2-(chlorocarbonyl)isonicotinate as yellow oil.

Workup

  1. customat 25-30° C.
  2. customfor 3 days
  3. customThe reaction was evaporated in vacuo

Sources & evidence

ORD record
ord-7c7ce70bf8ef4a458789e6506beafe38
Source dataset
uspto-grants-2014_08
Patent number
US08802690B2

Reaction notes

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