Methanol → HCID 13958508, compound

HRID 255983Notes

Reaction equation

HRID 255983 reaction equation
[CH2:1]([N:3]1[C:12]2[C:7](=[CH:8][C:9]([F:21])=[C:10]([C:13]3[CH:18]=[C:17]([CH3:19])[N:16]=[C:15]([CH3:20])[CH:14]=3)[CH:11]=2)[C:6](=[O:22])[C:5]([C:23]([O:25]CC)=[O:24])=[CH:4]1)[CH3:2].[OH-].[Na+].O.CO>C(O)(=O)C>[CH2:1]([N:3]1[C:12]2[C:7](=[CH:8][C:9]([F:21])=[C:10]([C:13]3[CH:18]=[C:17]([CH3:19])[N:16]=[C:15]([CH3:20])[CH:14]=3)[CH:11]=2)[C:6](=[O:22])[C:5]([C:23]([OH:25])=[O:24])=[CH:4]1)[CH3:2]

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 14798Sodium HydroxideHCID 13958509HCID 13958509, compound

Product 1

HCID 13958508HCID 13958508, compoundYield 95.9%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture containing 98 g of ethyl 1-ethyl-6-fluoro-1,4-dihydro-7-(2,6-dimethyl-4-pyridinyl)-4-oxo-3-quinolinecarboxylate, 50 ml of 35% aqueous sodium hydroxide solution, 500 ml of water and 100 ml of methanol was refluxed with stirring for 90 minutes and the resulting brown solution was acidified with acetic acid whereupon a light yellow precipitate separated. The mixture was allowed to stand at room temperature for about 2 hours and the precipitate was collected, washed successively with water and ethanol and then dried at 90°-95° C. to yield 86.8 g (95%) of 1-ethyl-6-fluoro-1,4-dihydro-7-(2,6-dimethyl-4-pyridinyl)-4-oxo-3-quinolinecarboxylic acid, m.p. >310° C.

Workup

  1. temperaturewas refluxed
  2. customseparated
  3. waitto stand at room temperature for about 2 hours
  4. customthe precipitate was collected
  5. washwashed successively with water and ethanol
  6. customdried at 90°-95° C.

Sources & evidence

ORD record
ord-1ae56b70638042d7b0009e2088656ac9
Source dataset
uspto-grants-1987_10
Patent number
US04699984

Reaction notes

Loading…