Dimethylformamide → HCID 178522869, compound

HRID 2289910Notes

Reaction equation

HRID 2289910 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][C:6]([C:12]([OH:14])=O)=[C:5]2[OH:15].CN(C)C=O.C(N1C=CN=C1)(N1C=CN=C1)=O.[Cl:33][C:34]1[CH:41]=[CH:40][C:37]([CH2:38][NH2:39])=[CH:36][CH:35]=1>O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][C:6]([C:12]([NH:39][CH2:38][C:37]1[CH:40]=[CH:41][C:34]([Cl:33])=[CH:35][CH:36]=1)=[O:14])=[C:5]2[OH:15]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 660364-ChlorobenzylamineHCID 682631,1'-CarbonyldiimidazoleHCID 178524714HCID 178524714, compound

Product 1

HCID 178522869HCID 178522869, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

To a mixture of 0.365 g of 6-chloro-4-hydroxy-3-quinolinecarboxylic acid (J. Amer. Chem. Soc., 68, 1264 (1946)) and 5 mL of dimethylformamide is added 0.29 g of carbonyldiimidazole. The mixture is stirred 18 h at 60° C. and then it is cooled to 25° C. To the resulting solution is added 0.22 mL of 4-chlorobenzylamine. After stirring for 18 hours the mixture is diluted with 10 mL of distilled water. After 30 minutes the precipitate is collected by filtration and it is washed with two successive mL portions of water. It is then washed with 5 mL of diethyl ether. It is dried for 48 h at 85° C. and 20 torr. This procedure yields the title compound as 251 mg of an off-white solid.

Workup

  1. temperatureit is cooled to 25° C
  2. stirringAfter stirring for 18 hours the mixture
  3. filtrationAfter 30 minutes the precipitate is collected by filtration and it
  4. washis washed with two successive mL portions of water
  5. washIt is then washed with 5 mL of diethyl ether
  6. customIt is dried for 48 h at 85° C.

Sources & evidence

ORD record
ord-6454c019c1d74e39afcd4ea318d0bbf3
Source dataset
uspto-grants-2000_07
Patent number
US06093732

Reaction notes

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