Water → HCID 178522880, compound

HRID 2289943Notes

Reaction equation

HRID 2289943 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([OH:15])=[C:7]([C:12]([OH:14])=O)[CH:8]=[N:9]2)=[CH:4][CH:3]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.O.[Cl:29][C:30]1[CH:37]=[CH:36][C:33]([CH2:34][NH2:35])=[CH:32][CH:31]=1>CN(C)C=O>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([OH:15])=[C:7]([C:12]([NH:35][CH2:34][C:33]3[CH:36]=[CH:37][C:30]([Cl:29])=[CH:31][CH:32]=3)=[O:14])[CH:8]=[N:9]2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 660364-ChlorobenzylamineHCID 682631,1'-CarbonyldiimidazoleHCID 178524720HCID 178524720, compound

Product 1

HCID 178522880HCID 178522880, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

7-Chloro-4-hydroxy-3-quinolinecarboxylic acid (500 mg) (Org. Syn. Coll. 3:272-275 (1955)) is dissolved in N,N-dimethylformamide (20 mL) and to the mixture is added 1,1'-carbonyl diimidazole (399 mg). The mixture is heated at 50° C. for 20 h and then allowed to cool to rt. The mixture is treated with water (200 mL) and then after 5 min, 4-chlorobenzylamine (300 mL) is added. The mixture is allowed to stir at rt for 2 days and then is poured into water (50 mL) and the resulting white precipitate is filtered. The crude product is recrystallized (acetic acid, water) to afford 481 mg of the title compound as a white solid.

Workup

  1. temperatureto cool to rt
  2. filtrationthe resulting white precipitate is filtered
  3. customThe crude product is recrystallized (acetic acid, water)

Sources & evidence

ORD record
ord-543d006bf4994814b72af89bd3c8cab4
Source dataset
uspto-grants-2000_07
Patent number
US06093732

Reaction notes

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