Acetonitrile → HCID 461444, compound

HRID 2418673Notes

Reaction equation

HRID 2418673 reaction equation
[CH2:1]([N:3]1[C:12]2[C:7](=[CH:8][C:9]([F:14])=[C:10](F)[CH:11]=2)[C:6](=[O:15])[C:5]([C:16]([OH:18])=[O:17])=[CH:4]1)[CH3:2].[NH:19]1[CH2:24][CH2:23][S:22][CH2:21][CH2:20]1.C(#N)C>CN(C)C=O>[CH2:1]([N:3]1[C:12]2[C:7](=[CH:8][C:9]([F:14])=[C:10]([N:19]3[CH2:24][CH2:23][S:22][CH2:21][CH2:20]3)[CH:11]=2)[C:6](=[O:15])[C:5]([C:16]([OH:18])=[O:17])=[CH:4]1)[CH3:2]

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 67164ThiomorpholineHCID 8005211-Ethyl-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

Product 1

HCID 461444HCID 461444, compoundYield 65.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 1.35 g (5.33 mmol) of 1-ethyl-6,7-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid, 1.34 ml (13.3 mmol) of thiomorpholine, 40 ml of acetonitrile, and 20 ml of N,N-dimethylformamide was heated under reflux for 21 hours. The reaction mixture was cooled to room temperature and the solid was collected by filtration, washed with water and acetonitrile, and dried to give 1.18 g of 1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(4-thiomorpholinyl)-3-quinolinecarboxylic acid, mp 254°-6°.

Workup

  1. temperatureunder reflux for 21 hours
  2. filtrationthe solid was collected by filtration
  3. washwashed with water and acetonitrile
  4. customdried

Sources & evidence

ORD record
ord-02a3ee294ecb42d5b6e021b0850ac5e3
Source dataset
uspto-grants-1984_09
Patent number
US04473568

Reaction notes

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