Oxalyl chloride → Quinoline-6-carbonyl chloride

HRID 1890544Notes

Reaction equation

HRID 1890544 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 (O-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-8d06c4701c524b6990bbddb8277a028b
Source dataset
uspto-grants-2013_08
Patent number
US08507487B2

Reaction notes

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