Oxalyl chloride → 2-Methylpyridine-3-carbonyl chloride--hydrogen chloride (1/1)

HRID 1604540Notes

Reaction equation

HRID 1604540 reaction equation
[CH3:1][C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4](O)=[O:5].C(Cl)(=O)C([Cl:14])=O>ClCCl.CN(C)C=O>[ClH:14].[CH3:1][C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([Cl:14])=[O:5]

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 6433732-Methylnicotinic acid

Product 1

HCID 183219202-Methylpyridine-3-carbonyl chloride--hydrogen chloride (1/1)Yield 169.9%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-methylnicotinic acid (470 mg) in dichloromethane (6 ml) were dropwise added oxalyl chloride (522 mg) and dimethylformamide (1 drop) at 0° C. under nitrogen atmosphere, and the mixture was stirred for 1 hour at the same condition. The mixture was concentrated and the residue was pulverized with diethyl ether to give 2-methylnicotinoyl chloride hydrochloride (671 mg) as a solid.

Workup

  1. customat 0° C.
  2. concentrationThe mixture was concentrated

Sources & evidence

ORD record
ord-f609be746f8340459aa6b5f40440d441
Source dataset
uspto-grants-1999_11
Patent number
US05994368

Reaction notes

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