Oxalyl chloride → HCID 90417622, compound

HRID 513944Notes

Reaction equation

HRID 513944 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:20]=[CH:21][CH:22]=1)[CH2:5][O:6][C:7]1[CH:16]=[C:15]2[C:10]([CH:11]=[C:12]([C:17](O)=[O:18])[CH:13]=[N:14]2)=[CH:9][CH:8]=1.C(Cl)(=O)C([Cl:26])=O>C(Cl)Cl.CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:20]=[CH:21][CH:22]=1)[CH2:5][O:6][C:7]1[CH:16]=[C:15]2[C:10]([CH:11]=[C:12]([C:17]([Cl:26])=[O:18])[CH:13]=[N:14]2)=[CH:9][CH:8]=1

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 90417158HCID 90417158, compound

Product 1

HCID 90417622HCID 90417622, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 7-((3-chlorobenzyl)oxy)quinoline-3-carboxylic acid (Example 46, product from Step A, 50 mg, 0.16 mmol) in DCM (1.5 mL) was added oxalyl chloride (0.1 mL, 1.13 mmol), followed by 1 drop of DMF. After 30 minutes the reaction was concentrated under reduced pressure to afford a yellow foam, and further dried under high vacuum for 15 minutes to afford the title compound, which was used without further purification in the next step.

Workup

  1. concentrationAfter 30 minutes the reaction was concentrated under reduced pressure
  2. customto afford a yellow foam
  3. customfurther dried under high vacuum for 15 minutes

Sources & evidence

ORD record
ord-9273cceec34b40a99dc52c75a34a7ae8
Source dataset
uspto-grants-2015_08
Patent number
US09102674B2

Reaction notes

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