4-Chlorobenzylamine → HCID 178503090, compound

HRID 2290050Notes

Reaction equation

HRID 2290050 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([S:12][CH3:13])=[CH:9][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>C(Cl)(Cl)Cl.CO>[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][CH:9]=[C:8]([S:12][CH3:13])[CH:7]=3)=[O:16])=[CH:22][CH:21]=1

Participants

5

Reactant 2

HCID 660364-ChlorobenzylamineHCID 178469641HCID 178469641, compound

Product 1

HCID 178503090HCID 178503090, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6212ChloroformSolvent

Procedure

A solution of 50 mg of ethyl 4-hydroxy-7-(methylsulfanyl)-3-quinolinecarboxylate in 200 μL of 4-chlorobenzylamine is heated at 190° C. under argon for 16 h, then cooled and diluted with CHCl3 and MeOH. The solution is washed with dil. HCl, dried (Na2SO4), and concentrated under reduced pressure to a yellow solid. Flash chromatography on silica using 2-4% MeOH in CH2Cl2 affords 62.4 mg (92%) of N-(4-chlorobenzyl)-4-hydroxy-7-(methylsulfanyl)-3-quinolinecarboxamide.

Workup

  1. temperaturecooled
  2. washThe solution is washed with dil. HCl
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated under reduced pressure to a yellow solid

Sources & evidence

ORD record
ord-7bb0f4b088644d38b48ac916657d64e4
Source dataset
uspto-grants-2000_07
Patent number
US06093732

Reaction notes

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