Dimethylformamide → HCID 178522922, compound

HRID 2289908Notes

Reaction equation

HRID 2289908 reaction equation
[F:1][C:2]1[C:11]([F:12])=[C:10]2[C:5]([C:6]([OH:16])=[C:7]([C:13]([OH:15])=O)[CH:8]=[N:9]2)=[CH:4][CH:3]=1.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:7]2[CH:8]=[N:9][C:10]3[C:5]([C:6]=2[OH:16])=[CH:4][CH:3]=[C:2]([F:1])[C:11]=3[F:12])=[O:15])=[CH:37][CH:36]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 660364-ChlorobenzylamineHCID 682631,1'-CarbonyldiimidazoleHCID 178524734HCID 178524734, compound

Product 1

HCID 178522922HCID 178522922, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

To a mixture of 0.25 g of 7,8-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 280 mg of a white powder.

Workup

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

Sources & evidence

ORD record
ord-f44c0c0489ef435ca96377703ca2a6c4
Source dataset
uspto-grants-2000_07
Patent number
US06093732

Reaction notes

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