4-Chlorobenzylamine → HCID 178522857, compound

HRID 2289896Notes

Reaction equation

HRID 2289896 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][C:3]=1[C:12]([O:14]CC)=O.[Cl:17][C:18]1[CH:25]=[CH:24][C:21]([CH2:22][NH2:23])=[CH:20][CH:19]=1>>[Cl:17][C:18]1[CH:25]=[CH:24][C:21]([CH2:22][NH:23][C:12]([C:3]2[CH:4]=[N:5][C:6]3[C:11]([C:2]=2[OH:1])=[CH:10][CH:9]=[CH:8][CH:7]=3)=[O:14])=[CH:20][CH:19]=1

Participants

3

Reactant 2

HCID 660364-ChlorobenzylamineHCID 178469510HCID 178469510, compound

Product 1

HCID 178522857HCID 178522857, compound

Conditions

Temperature
200 °C

Procedure

A mixture of 0.50 g of ethyl 4-hydroxy-3-quinolinecarboxylate (J. Amer. Chem. Soc., 68, 1264 (1946)) and 5.0 mL of 4-chlorobenzylamine is stirred 18 h 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 at 20 torr and 45° C. for 18 h. The yield is 0.28 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 at 20 torr and 45° C. for 18 h

Sources & evidence

ORD record
ord-3489bbbca31a4b789c21dc236ab1240a
Source dataset
uspto-grants-2000_07
Patent number
US06093732

Reaction notes

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