Oxalyl chloride → 6-Methylnicotinoyl chloride

HRID 589397Notes

Reaction equation

HRID 589397 reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](O)=[O:7])=[CH:4][N:3]=1.C(Cl)(=O)C([Cl:14])=O>ClCCl.CN(C)C=O>[CH3:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([Cl:14])=[O:7])=[CH:4][N:3]=1

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 1378606-Methylnicotinic acid

Product 1

HCID 218904586-Methylnicotinoyl chloride

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

6-Methyl nicotinic acid (138 mg, 1.00 mmol) was dissolved in dichloromethane (15 mL) and N,N-dimethylformamide (0.10 mL), and in an ice bath oxalic chloride (192 mg, 1.51 mmol) was added dropwise slowly. Upon completion of the dropwise addition, it was moved to react at room temperature for 3 hours, and concentrated under reduce pressure to obtain 6-methyl nicotinoyl chloride as a white solid.

Workup

  1. additionUpon completion of the dropwise addition, it
  2. customto react at room temperature for 3 hours
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-9a433cafe5f24ab28e3d3a27ecdb497b
Source dataset
uspto-grants-2016_01
Patent number
US09233098B2

Reaction notes

Loading…