4-Chlorobenzylamine → HCID 178522882, compound

HRID 2290034Notes

Reaction equation

HRID 2290034 reaction equation
C([O:4][CH2:5][CH2:6][NH:7][C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][CH:17]=1)[N:14]=[CH:13][C:12]([C:18]([O:20]CC)=O)=[C:11]2[OH:23])(=O)C.[Cl:24][C:25]1[CH:32]=[CH:31][C:28]([CH2:29][NH2:30])=[CH:27][CH:26]=1>>[Cl:24][C:25]1[CH:32]=[CH:31][C:28]([CH2:29][NH:30][C:18]([C:12]2[CH:13]=[N:14][C:15]3[C:10]([C:11]=2[OH:23])=[CH:9][C:8]([NH:7][CH2:6][CH2:5][OH:4])=[CH:17][CH:16]=3)=[O:20])=[CH:27][CH:26]=1

Participants

3

Reactant 2

HCID 660364-ChlorobenzylamineHCID 178469578HCID 178469578, compound

Product 1

HCID 178522882HCID 178522882, compound

Conditions

Temperature
160 °C

Procedure

To a flask containing ethyl 6-{[2-(acetyloxy)ethyl]amino)-4-hydroxy-3-quinolinecarboxylate (0.04 g) is added p-chlorobenzylamine (0.5 mL). The reaction is tightly capped and heated to 160° C. overnight. The reaction is cooled to room temperature, adsorbed onto silica and chromatographed on silica eluting with 3% to 10% methanol in dichloromethane. The product-containing fractions are evaporated to give 0.02 g of the title compound as a yellow solid.

Workup

  1. customThe reaction is tightly capped
  2. temperatureThe reaction is cooled to room temperature
  3. customchromatographed on silica eluting with 3% to 10% methanol in dichloromethane
  4. customThe product-containing fractions are evaporated

Sources & evidence

ORD record
ord-c936b8ca35b245ec81e29fc07a3a6f29
Source dataset
uspto-grants-2000_07
Patent number
US06093732

Reaction notes

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