Oxalyl chloride → 3-Methyloxy-2-phenyl-4-quinolinecarbonyl chloride

HRID 1455516Notes

Reaction equation

HRID 1455516 reaction equation
[CH3:1][O:2][C:3]1[C:4]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[N:5][C:6]2[C:11]([C:12]=1[C:13](O)=[O:14])=[CH:10][CH:9]=[CH:8][CH:7]=2.C(Cl)(=O)C([Cl:25])=O>C(Cl)Cl>[CH3:1][O:2][C:3]1[C:4]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[N:5][C:6]2[C:11]([C:12]=1[C:13]([Cl:25])=[O:14])=[CH:10][CH:9]=[CH:8][CH:7]=2

Participants

4

Reactant 2

HCID 65578Oxalyl chlorideHCID 6243483-Methoxy-2-phenylquinoline-4-carboxylic acid

Product 1

HCID 213546903-Methyloxy-2-phenyl-4-quinolinecarbonyl chloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-Methyloxy-2-phenylquinoline-4-carboxylic acid (200 mg, 0.72 mmol) [J. Med. Chem. 1999, 42, 1053-1065] was suspended in CH2Cl2 (5 mL) at 0° C. and oxalyl chloride (62 μL, 0.72 mmol) was added with stirring. After stirring at 0° C. for 1 h the cooling bath was removed and the solution allowed to stir at room temperature for 18 h. After this time the solvent was evaporated and the crude acid chloride used in the subsequent reaction without further purification.

Workup

  1. stirringAfter stirring at 0° C. for 1 h the cooling bath
  2. customwas removed
  3. stirringto stir at room temperature for 18 h
  4. customAfter this time the solvent was evaporated
  5. customthe crude acid chloride used in the subsequent reaction without further purification

Sources & evidence

ORD record
ord-12ece4c756da4312bd7c9d805b68b55c
Source dataset
uspto-grants-2009_01
Patent number
US07482457B2

Reaction notes

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