Oxalyl chloride → Quinoline-6-carbonyl chloride

HRID 876790

Reaction equation

HRID 876790 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][C:7]([C:11]([OH:13])=O)=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.C(Cl)(=O)C([Cl:17])=O>C(Cl)Cl.CN(C=O)C>[N:1]1[C:10]2[C:5](=[CH:6][C:7]([C:11]([Cl:17])=[O:13])=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 825716-Quinolinecarboxylic acid

Product 1

HCID 12391963Quinoline-6-carbonyl chlorideYield 99.8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a mixture of quinoline-6-carboxylic acid (0-1) (2.0 g, 11.5 mmol) in CH2Cl2 (250 mL) was added 3 drops of DMF at 0° C., followed by oxalyl chloride (7.3 g, 57.5 mmol) dropwise. The resulting reaction was stirred at room temperature overnight, and then concentrated to afford the title compound (2.2 g).

Workup

  1. customThe resulting reaction
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-a32c4c7516d54483ba9baf7d0922695d
Source dataset
uspto-grants-2015_03
Patent number
US08987269B2

Linked notes

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