Oxalyl chloride → HCID 90416631, compound

HRID 1748407Notes

Reaction equation

HRID 1748407 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:23]=[CH:24][CH:25]=1)[CH2:5][O:6][C:7]1[CH:16]=[C:15]2[C:10]([CH:11]=[C:12]([C:17]([CH3:22])([CH3:21])[C:18](O)=[O:19])[CH:13]=[N:14]2)=[CH:9][CH:8]=1.C(Cl)(=O)C([Cl:29])=O>C(Cl)Cl.CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:23]=[CH:24][CH:25]=1)[CH2:5][O:6][C:7]1[CH:16]=[C:15]2[C:10]([CH:11]=[C:12]([C:17]([CH3:22])([CH3:21])[C:18]([Cl:29])=[O:19])[CH:13]=[N:14]2)=[CH:9][CH:8]=1

Participants

5

Reactant 2

HCID 65578Oxalyl chloride2×HCID 90417364HCID 90417364, compound

Product 1

HCID 90416631HCID 90416631, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(7-((3-chlorobenzyl)oxy)quinolin-3-yl)-2-methylpropanoic acid in DCM (8 mL) was added oxalyl chloride (208 μL, 2.34 mmol) followed by 3 drops of DMF. After 30 minutes, additional oxalyl chloride (2 mL, 22.5 mmol) was added. After 30 minutes stifling at ambient temperature the reaction was concentrated under reduced pressure and dried under high vacuum to afford the title compound as an oil. The crude product was used without further purification in the next step.

Workup

  1. waitAfter 30 minutes stifling at ambient temperature
  2. concentrationthe reaction was concentrated under reduced pressure
  3. customdried under high vacuum

Sources & evidence

ORD record
ord-318c271935c745ae8852136a631958fa
Source dataset
uspto-grants-2015_10
Patent number
US09150572B2

Reaction notes

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