Oxalyl chloride → HCID 90416631, compound

HRID 513957Notes

Reaction equation

HRID 513957 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-6ab5a1ec5e384300b1644b3c8b15a70b
Source dataset
uspto-grants-2015_08
Patent number
US09102674B2

Reaction notes

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