Methanol → HCID 86736428, compound

HRID 614774Notes

Reaction equation

HRID 614774 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([CH3:12])[CH:11]=1)[N:8]([CH2:13][C:14]([F:17])([F:16])[F:15])[CH:7]=[C:6]([C:18]([OH:20])=[O:19])[C:5]2=[O:21].S(Cl)(Cl)=O.[CH3:26]O.O>N1C=CC=CC=1>[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([CH3:12])[CH:11]=1)[N:8]([CH2:13][C:14]([F:17])([F:16])[F:15])[CH:7]=[C:6]([C:18]([O:20][CH3:26])=[O:19])[C:5]2=[O:21]

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 24386Thionyl ChlorideHCID 21327117HCID 21327117, compound

Product 1

HCID 86736428HCID 86736428, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 2.3 g of 6-fluoro-1,4-dihydro-8-methyl-4-oxo-1-(2,2,2-trifluoroethyl)-3-quinolinecarboxylic acid in 25 ml of pyridine, at 0°, was added 1.1 ml of thionyl chloride. The resulting slurry was stirred at room temperature for 0.5 hour and subsequently treated with 5 ml of methanol. After 1 hour, the reaction mixture was poured into 200 ml of water; the resulting white solid was filtered, washed with water, and dried to give 2.0 g of 6-fluoro-1,4-dihydro-8-methyl-4-oxo-1-(2,2,2-trifluoroethyl)-3-quinolinecarboxylic acid, methyl ester, m.p. 168°-171°.

Workup

  1. waitAfter 1 hour
  2. filtrationthe resulting white solid was filtered
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-a606034e31ed4e90834cef610bf1ec93
Source dataset
uspto-grants-1979_03
Patent number
US04146625

Reaction notes

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