4-Chlorobenzylamine → HCID 178522881, compound

HRID 2290037Notes

Reaction equation

HRID 2290037 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([N:12]3[CH2:16][CH2:15][O:14][C:13]3=[O:17])[CH:10]=2)[N:5]=[CH:4][C:3]=1[C:18]([O:20]CC)=O.[Cl:23][C:24]1[CH:31]=[CH:30][C:27]([CH2:28][NH2:29])=[CH:26][CH:25]=1>>[Cl:23][C:24]1[CH:31]=[CH:30][C:27]([CH2:28][NH:29][C:18]([C:3]2[CH:4]=[N:5][C:6]3[C:11]([C:2]=2[OH:1])=[CH:10][C:9]([N:12]2[CH2:16][CH2:15][O:14][C:13]2=[O:17])=[CH:8][CH:7]=3)=[O:20])=[CH:26][CH:25]=1

Participants

3

Reactant 2

HCID 660364-ChlorobenzylamineHCID 178469570HCID 178469570, compound

Product 1

HCID 178522881HCID 178522881, compound

Conditions

Temperature
185 °C

Procedure

To a flask containing ethyl 4-hydroxy-6-(2-oxo-1,3-oxazolidin-3-yl)-3-quinolinecarboxylate (0.17 g) is added p-chlorobenzylamine (1.0 mL). The reaction is tightly capped and heated to 185° C. over 1 hour. The reaction is cooled to room temperature and triturated with diethyl ether. The residue is adsorbed onto silica and chromatographed on silica eluting with 3% to 12% methanol in dichloromethane. The product-containing fractions are evaporated to give 0.12 g of the title compound as a off-white solid.

Workup

  1. customThe reaction is tightly capped
  2. temperatureThe reaction is cooled to room temperature
  3. customtriturated with diethyl ether
  4. customchromatographed on silica eluting with 3% to 12% methanol in dichloromethane
  5. customThe product-containing fractions are evaporated

Sources & evidence

ORD record
ord-5752c724e84e48eb9b13c22f80416422
Source dataset
uspto-grants-2000_07
Patent number
US06093732

Reaction notes

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