Oxalyl chloride → HCID 18979085, compound

HRID 1108597Notes

Reaction equation

HRID 1108597 reaction equation
[CH3:1][O:2][C:3]1[C:12]2[N:11]=[CH:10][CH:9]=[CH:8][C:7]=2[C:6]([C:13]([OH:15])=O)=[CH:5][CH:4]=1.C(Cl)(=O)C([Cl:19])=O>ClCCl.CN(C)C=O>[ClH:19].[CH3:1][O:2][C:3]1[C:12]2[N:11]=[CH:10][CH:9]=[CH:8][C:7]=2[C:6]([C:13]([Cl:19])=[O:15])=[CH:5][CH:4]=1

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 102622888-methoxyquinoline-5-carboxylic Acid

Product 1

HCID 18979085HCID 18979085, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

A suspension of 8-methoxyquinoline-5-carboxylic acid (5.0 g) in dichloromethane (50 ml) was cooled to 20 C. Oxalyl chloride (4.29 ml) was added cautiously and then dry dimethylformamide (8 drops) was added dropwise. The mixture was stirred at 0° C. for 1h and then at room temperature for 24h. The solvent was removed in vacuo and the residue azeotroped with a small amount of toluene. The title compound was obtained as a brown solid (5.18 g).

Workup

  1. temperaturewas cooled to 20 C
  2. customThe solvent was removed in vacuo
  3. customthe residue azeotroped with a small amount of toluene

Sources & evidence

ORD record
ord-a001225a9c634ca38bea9d3db0dc6281
Source dataset
uspto-grants-2000_05
Patent number
US06069151

Reaction notes

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