4-Chlorobenzylamine → HCID 178522897, compound

HRID 2290047Notes

Reaction equation

HRID 2290047 reaction equation
[CH2:1]([S:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([OH:24])=[C:14]([C:19]([O:21]CC)=O)[CH:15]=[N:16]2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:25][C:26]1[CH:33]=[CH:32][C:29]([CH2:30][NH2:31])=[CH:28][CH:27]=1>>[CH2:1]([S:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([OH:24])=[C:14]([C:19]([NH:31][CH2:30][C:29]3[CH:32]=[CH:33][C:26]([Cl:25])=[CH:27][CH:28]=3)=[O:21])[CH:15]=[N:16]2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 660364-ChlorobenzylamineHCID 178469640HCID 178469640, compound

Product 1

HCID 178522897HCID 178522897, compoundYield 92.4%

Procedure

A mixture of 4.07 g of ethyl 7-(benzylsulfanyl)-4-hydroxy-3-quinolinecarboxylate from Preparation No. 29 and 8.5 g of 4-chlorobenzylamine is heated at 165° C. for 18 h, then cooled and partitioned between 1 N HCl and chloroform-methanol. The organic phase is dried (MgSO4) and concentrated under reduced pressure, and the residue flash chromatographed on silica using 2-5% methanol in dichloromethane to provide 4.82 g of the title compound.

Workup

  1. customfrom Preparation No
  2. temperaturecooled
  3. custompartitioned between 1 N HCl and chloroform-methanol
  4. dry with materialThe organic phase is dried (MgSO4)
  5. concentrationconcentrated under reduced pressure
  6. customthe residue flash chromatographed on silica using 2-5% methanol in dichloromethane

Sources & evidence

ORD record
ord-046d4272f5e64841b9957250dfe6cb3c
Source dataset
uspto-grants-2000_07
Patent number
US06093732

Reaction notes

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