Methanol → HCID 136338336, compound

HRID 245212Notes

Reaction equation

HRID 245212 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[OH:12])[N:8]=[C:7]([C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([F:22])([F:21])[F:20])[CH:14]=1)[C:6]([CH3:23])=[C:5]2[C:24]([OH:26])=[O:25].[C:27](Cl)(=O)C(Cl)=O.CO>ClCCl.CN(C=O)C>[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[OH:12])[N:8]=[C:7]([C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([F:22])([F:20])[F:21])[CH:14]=1)[C:6]([CH3:23])=[C:5]2[C:24]([O:26][CH3:27])=[O:25]

Participants

6

Reactant 3

HCID 887MethanolHCID 65578Oxalyl chloride2×HCID 136338343HCID 136338343, compound

Product 1

HCID 136338336HCID 136338336, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a suspension of 6-fluoro-7-hydroxy-3-methyl-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylic acid (9.0 g, 24.64 mmol) in dichloromethane (120 mL) at 0° C. was added 5 drops of DMF. Oxalyl chloride (3.24 mL, 37.0 mmol) was added slowly. The mixture was stirred at 0° C. for 1 h. The mixture was warmed to room temperature, and an additional portion of oxalyl chloride (3.24 mL, 37.0 mmol) was added. The reaction mixture was stirred overnight. Methanol (50 mL) was added and the mixture was stirred overnight. The solvent was removed under reduced pressure to afford methyl 6-fluoro-7-hydroxy-3-methyl-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylate. This material was used without further purification in the next step. MS (m/z) 380.1 (M+H+).

Workup

  1. temperatureThe mixture was warmed to room temperature
  2. stirringThe reaction mixture was stirred overnight
  3. stirringthe mixture was stirred overnight
  4. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-d80c10603faf493aa67228ffad493ab2
Source dataset
uspto-grants-2014_02
Patent number
US08658636B2

Reaction notes

Loading…