4-Chlorobenzylamine → HCID 178487897, compound

HRID 2289912Notes

Reaction equation

HRID 2289912 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][C:3]=1[C:14]([O:16]CC)=O.[Cl:19][C:20]1[CH:27]=[CH:26][C:23]([CH2:24][NH2:25])=[CH:22][CH:21]=1>C1(C)C=CC=CC=1>[Cl:19][C:20]1[CH:27]=[CH:26][C:23]([CH2:24][NH:25][C:14]([C:3]2[CH:4]=[N:5][C:6]3[C:11]([C:2]=2[OH:1])=[CH:10][C:9]([O:12][CH3:13])=[CH:8][CH:7]=3)=[O:16])=[CH:22][CH:21]=1

Participants

4

Reactant 2

HCID 660364-ChlorobenzylamineHCID 178469588HCID 178469588, compound

Product 1

HCID 178487897HCID 178487897, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
210 °C

Procedure

A mixture of 320 mg of ethyl 4-hydroxy-6-methoxy-3-quinolinecarboxylate (J. Amer. Chem. Soc., 68, 1204 (1946)) and 1.0 mL of 4-chlorobenzylamine is stirred for 1 h at 210° C. The mixture is cooled to 25° C. and it is diluted with 2.0 mL of toluene. The mixture is filtered and the filtrant is dissolved in a minimum volume of refluxing glacial acetic acid. The hot solution is treated with distilled water dropwise until it becomes cloudy, and it is allowed to cool to 25° C. The precipitate is collected by filtration and it is washed with a small amount of dilute aqueous acetic acid. It is dried in a stream of air and then it is dissolved in 7 mL of refluxing acetonitrile. The solution is allowed to cool to 25° C. and after an additional 2 h the precipitate is collected by filtration. The solid is dried for 48 h at torr and 85° C. This procedure gives the title compound as 64 mg of a light tan solid.

Workup

  1. temperatureThe mixture is cooled to 25° C.
  2. filtrationThe mixture is filtered
  3. dissolutionthe filtrant is dissolved in a minimum volume of refluxing glacial acetic acid
  4. additionThe hot solution is treated with distilled water dropwise until it
  5. temperatureto cool to 25° C
  6. filtrationThe precipitate is collected by filtration and it
  7. washis washed with a small amount of dilute aqueous acetic acid
  8. customIt is dried in a stream of air
  9. dissolutionit is dissolved in 7 mL of refluxing acetonitrile
  10. temperatureto cool to 25° C. and after an additional 2 h the precipitate
  11. filtrationis collected by filtration
  12. customThe solid is dried for 48 h at torr and 85° C

Sources & evidence

ORD record
ord-47a7fb62419541eda06d7f43ace31bcc
Source dataset
uspto-grants-2000_07
Patent number
US06093732

Reaction notes

Loading…