4-Chlorobenzylamine → HCID 178522919, compound

HRID 2290041Notes

Reaction equation

HRID 2290041 reaction equation
[CH2:1]([S:8][C:9]1[CH:10]=[C:11]2[C:16](=[C:17]([F:19])[CH:18]=1)[N:15]=[CH:14][C:13]([C:20]([O:22]CC)=O)=[C:12]2[OH:25])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:26][C:27]1[CH:34]=[CH:33][C:30]([CH2:31][NH2:32])=[CH:29][CH:28]=1>C(Cl)(Cl)Cl.CO>[CH2:1]([S:8][C:9]1[CH:10]=[C:11]2[C:16](=[C:17]([F:19])[CH:18]=1)[N:15]=[CH:14][C:13]([C:20]([NH:32][CH2:31][C:30]1[CH:33]=[CH:34][C:27]([Cl:26])=[CH:28][CH:29]=1)=[O:22])=[C:12]2[OH:25])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 660364-ChlorobenzylamineHCID 178469649HCID 178469649, compound

Product 1

HCID 178522919HCID 178522919, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6212ChloroformSolvent

Procedure

A solution of 3.93 g of of ethyl 6-(benzylsulfanyl)-8-fluoro-4-hydroxy-3-quinolinecarboxylate in 8.8 g of 4-chlorobenzylamine is heated at 165° 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 3-6% MeOH in CH2Cl2 affords 4.73 g (95%) of 6-(benzylsulfanyl)-N-(4-chlorobenzyl)-8-fluoro-4-hydroxy-3-quinolinecarboxamide as a yellow solid.

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-4eb8345b2d38449ea4cf4de38791b130
Source dataset
uspto-grants-2000_07
Patent number
US06093732

Reaction notes

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