Acetonitrile → HCID 13339906, compound

HRID 2418672Notes

Reaction equation

HRID 2418672 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].[S:19]1[CH2:23][CH2:22][NH: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:21]3[CH2:22][CH2:23][S:19][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 10444ThiazolidineHCID 8005211-Ethyl-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

Product 1

HCID 13339906HCID 13339906, compoundYield 10.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 1.01 g (4.0 mmol) of 1-ethyl-6,7-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid, 0.79 ml (10 mmol) of thiazolidine, 20 ml of acetonitrile and 20 ml of N,N-dimethylformamide was heated at reflux for 16 hours. The reaction was cooled to room temperature and the solid which formed was removed by filtration. After triturating with hot methanol, the residue was recrystallized from N,N-dimethylformamide to give 0.13 g of 1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(3-thiazolidinyl)-3-quinolinecarboxylic acid; mp 270°-273° C.

Workup

  1. temperatureat reflux for 16 hours
  2. customthe solid which formed
  3. customwas removed by filtration
  4. customAfter triturating with hot methanol
  5. customthe residue was recrystallized from N,N-dimethylformamide

Sources & evidence

ORD record
ord-a73e241a13ba46348fb733c2f79b54f7
Source dataset
uspto-grants-1984_09
Patent number
US04473568

Reaction notes

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