Potassium Carbonate → HCID 19876843, compound

HRID 1886094Notes

Reaction equation

HRID 1886094 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[CH2:11][CH:12]1[CH2:20][C:19]2[C:14](=[CH:15][C:16]([OH:21])=[CH:17][CH:18]=2)[C:13]1=[O:22])([O:3][CH3:4])=[O:2].Br[CH2:24][C:25]1[CH:34]=[CH:33][C:32]2[C:27](=[CH:28][C:29]([Cl:35])=[CH:30][CH:31]=2)[N:26]=1.C([O-])([O-])=O.[K+].[K+]>CC(C)=O>[Cl:35][C:29]1[CH:28]=[C:27]2[C:32]([CH:33]=[CH:34][C:25]([CH2:24][O:21][C:16]3[CH:15]=[C:14]4[C:19]([CH2:20][CH:12]([CH2:11][C:6]5[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=5[C:1]([O:3][CH3:4])=[O:2])[C:13]4=[O:22])=[CH:18][CH:17]=3)=[N:26]2)=[CH:31][CH:30]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 102441602-(Bromomethyl)-7-chloroquinolineHCID 19876841HCID 19876841, compound

Product 1

HCID 19876843HCID 19876843, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of the product of Step 3 (17.5 g, 59 mmol), 2-bromomethyl-7-chloroquinoline (16.65 g, 65 mmol) and K2CO3 (8.97 g, 65 mmol) in acetone (200 ml) was refluxed for 14 hrs. The mixture was filtered and the filtrate was concentrated in vacuo. Chromatography of the resulting crude product on silica gel (eluted with 30% EtOAc/hexane) gave 21.15 g(80%) of the title compound.

Workup

  1. temperaturewas refluxed for 14 hrs
  2. filtrationThe mixture was filtered
  3. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-d30de2bc772043668b1ae2da742c85d3
Source dataset
uspto-grants-1992_09
Patent number
US05149703

Reaction notes

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