Dimethylformamide → HCID 178522913, compound

HRID 2289907Notes

Reaction equation

HRID 2289907 reaction equation
[F:1][C:2]1[CH:11]=[CH:10][C:9]([F:12])=[C:8]2[C:3]=1[C:4]([OH:16])=[C:5]([C:13]([OH:15])=O)[CH:6]=[N:7]2.CN(C)C=O.C(N1C=CN=C1)(N1C=CN=C1)=O.[Cl:34][C:35]1[CH:42]=[CH:41][C:38]([CH2:39][NH2:40])=[CH:37][CH:36]=1>O>[Cl:34][C:35]1[CH:42]=[CH:41][C:38]([CH2:39][NH:40][C:13]([C:5]2[CH:6]=[N:7][C:8]3[C:3]([C:4]=2[OH:16])=[C:2]([F:1])[CH:11]=[CH:10][C:9]=3[F:12])=[O:15])=[CH:37][CH:36]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 660364-ChlorobenzylamineHCID 682631,1'-CarbonyldiimidazoleHCID 178524733HCID 178524733, compound

Product 1

HCID 178522913HCID 178522913, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

To a mixture of 0.25 g of 5,8-difluoro-4-hydroxy-3-quinolinecarboxylic acid and 10 mL of dimethyformamide is added 0.20 g of carbonyldiimidazole. The mixture is stirred 18 h at 50° C. and then it is cooled to 25° C. The mixture is treated with 0.10 mL of distilled water and stirred for 5 min. To the resulting solution is added 0. 15 mL of 4-chlorobenzylamine. After stirring for 18 hours the solvent is evaporated at reduced pressure and the residue is dissolved in 10 mL of refluxing glacial acetic acid. Hot (100° C.) water is added dropwise until the solution becomes cloudy, and the mixture is allowed to cool to 25° C. The precipitate is collected by filtration and it is washed with two successive 5 mL portions of 50% aqueous acetic acid. It is dried for 18 h at 20 torr and 90° C. This procedure yields the title compound as 173 mg of a white powder.

Workup

  1. temperatureit is cooled to 25° C
  2. stirringstirred for 5 min
  3. additionTo the resulting solution is added 0
  4. stirringAfter stirring for 18 hours the solvent
  5. customis evaporated at reduced pressure
  6. dissolutionthe residue is dissolved in 10 mL of refluxing glacial acetic acid
  7. additionHot (100° C.) water is added dropwise until the solution
  8. temperatureto cool to 25° C
  9. filtrationThe precipitate is collected by filtration and it
  10. washis washed with two successive 5 mL portions of 50% aqueous acetic acid
  11. customIt is dried for 18 h at 20 torr and 90° C

Sources & evidence

ORD record
ord-de4ee6bd539b434999fa9e3fc17e4a9e
Source dataset
uspto-grants-2000_07
Patent number
US06093732

Reaction notes

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