Potassium Carbonate → HCID 15411291, compound

HRID 1418864Notes

Reaction equation

HRID 1418864 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][C:7](=O)[CH2:8][NH:9]2)=[CH:4][CH:3]=1.C([O-])([O-])=[O:14].[K+].[K+].[Cl:19][C:20]1[CH:29]=[C:28]2[C:23]([CH:24]=[CH:25][C:26]([CH2:30][O:31][C:32]3[CH:33]=[C:34]([CH:37]=[CH:38][CH:39]=3)[CH2:35]Cl)=[N:27]2)=[CH:22][CH:21]=1>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C=O)C>[Cl:19][C:20]1[CH:29]=[C:28]2[C:23]([CH:24]=[CH:25][C:26]([CH2:30][O:31][C:32]3[CH:33]=[C:34]([CH:37]=[CH:38][CH:39]=3)[CH2:35][O:1][C:2]3[CH:11]=[C:10]4[C:5]([CH2:6][CH2:7][C:8](=[O:14])[NH:9]4)=[CH:4][CH:3]=3)=[N:27]2)=[CH:22][CH:21]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 19369487HCID 19369487, compoundHCID 19369495HCID 19369495, compound

Product 1

HCID 15411291HCID 15411291, compoundYield 27.5%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 6228DimethylformamideSolvent

Procedure

A mixture of 0.326 g (2 mmol) of 7-hydroxy-1,2,3,4-tetrahydroquinolin-3-one, 0.609 g (5 mmol) of K2CO3, 0.075 g (0.25 mmol) of tetra-n-butylammonium bromide, 40 ml of DMF and 0.636 g (2 mmol) of 3-(7-chloro-2-quinolinylmethoxy)benzyl chloride was stirred at room temperature for 3 days. Insoluble matter was removed and the solvent was then distilled off. The residue was subjected to chromatography on a silica gel column. Subsequent to elution with CHCl3, recrystalization was conducted from acetone, whereby 0.245 g of the title compound was obtained as pale yellow powder (yield: 27.6%).

Workup

  1. customInsoluble matter was removed
  2. distillationthe solvent was then distilled off
  3. washSubsequent to elution
  4. customwith CHCl3, recrystalization

Sources & evidence

ORD record
ord-c92b4a6e11c04e70bc906e555b687086
Source dataset
uspto-grants-1999_03
Patent number
US05885987

Reaction notes

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