Oxalyl chloride → Quinoline-3-carbonyl Chloride

HRID 1166140Notes

Reaction equation

HRID 1166140 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]([C:11]([OH:13])=O)[CH:2]=1.C(Cl)(=O)C([Cl:17])=O>ClCCl.CN(C=O)C>[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]([C:11]([Cl:17])=[O:13])[CH:2]=1

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 80971Quinoline-3-carboxylic acid

Product 1

HCID 11030631Quinoline-3-carbonyl Chloride

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a suspension of 3-quinolinecarboxylic acid (580 mg, 3.35 mmol) in dichloromethane (25 mL) was added oxalyl chloride (2M in CH2Cl2, 3.4 mL, 6.7 mmol) dropwise at room temperature. DMF (1 drop) was added, resulting in immediate gas formation. The reaction mixture was stirred at room temperature for 2 h. Dichloromethane was evaporated. Additional dichloromethane (20 mL) was added to the residue. Concentration of the organic solvent gave the crude product. (640 mg, 99%).

Workup

  1. customresulting in immediate gas formation
  2. customDichloromethane was evaporated
  3. additionAdditional dichloromethane (20 mL) was added to the residue

Sources & evidence

ORD record
ord-cf4121c1fd5540f6baa7d4341bdba3b1
Source dataset
uspto-grants-2003_09
Patent number
US06613747B2

Reaction notes

Loading…