4-Chlorobenzylamine → HCID 178522901, compound

HRID 2289902Notes

Reaction equation

HRID 2289902 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][C:8]([C:12]([O:14]CC)=O)=[C:7]2[OH:17].[Cl:18][C:19]1[CH:26]=[CH:25][C:22]([CH2:23][NH2:24])=[CH:21][CH:20]=1>>[Cl:18][C:19]1[CH:26]=[CH:25][C:22]([CH2:23][NH:24][C:12]([C:8]2[CH:9]=[N:10][C:11]3[C:6]([C:7]=2[OH:17])=[CH:5][CH:4]=[CH:3][C:2]=3[F:1])=[O:14])=[CH:21][CH:20]=1

Participants

3

Reactant 2

HCID 660364-ChlorobenzylamineHCID 178469645HCID 178469645, compound

Product 1

HCID 178522901HCID 178522901, compound

Conditions

Temperature
200 °C

Procedure

A mixture of 0.50 g of ethyl 8-fluoro-4-hydroxy-3-quinolinecarboxylate (J. Med. Chem., 22, 816 (1979)) and 3.0 mL of 4-chlorobenzylamine is stirred 1 hour at 200° C. The mixture is cooled to 25° C. and it is diluted with 25 mL of hexanes. After stirring for an additional 1 h the solid precipitate is collected by filtration and washed with 10 mL of hexanes. It is dried in a stream of air and then it is suspended in 20 mL of glacial acetic acid. The mixture is heated until the solid is completely dissolved and the resulting solution is diluted with 200 mL of distilled water. The mixture is allowed to cool to 25° C. and the solid is collected by filtration. It is washed with a small volume of 10% aqueous acetic acid and then it is dried at torr and 45° C. for 18 h. The yield is 0.52 g.

Workup

  1. temperatureThe mixture is cooled to 25° C.
  2. stirringAfter stirring for an additional 1 h the solid precipitate
  3. filtrationis collected by filtration
  4. washwashed with 10 mL of hexanes
  5. customIt is dried in a stream of air
  6. temperatureThe mixture is heated until the solid
  7. dissolutionis completely dissolved
  8. additionthe resulting solution is diluted with 200 mL of distilled water
  9. temperatureto cool to 25° C.
  10. filtrationthe solid is collected by filtration
  11. washIt is washed with a small volume of 10% aqueous acetic acid
  12. customit is dried at torr and 45° C. for 18 h

Sources & evidence

ORD record
ord-379a2075271b4f91ad2819bc20642941
Source dataset
uspto-grants-2000_07
Patent number
US06093732

Reaction notes

Loading…