Dimethylformamide → HCID 15411291, compound

HRID 1292148Notes

Reaction equation

HRID 1292148 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.[Cl:13][C:14]1[CH:23]=[C:22]2[C:17]([CH:18]=[CH:19][C:20]([CH2:24][O:25][C:26]3[CH:27]=[C:28]([CH:31]=[CH:32][CH:33]=3)[CH2:29]Cl)=[N:21]2)=[CH:16][CH:15]=1.CN(C=[O:38])C>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[Cl:13][C:14]1[CH:23]=[C:22]2[C:17]([CH:18]=[CH:19][C:20]([CH2:24][O:25][C:26]3[CH:27]=[C:28]([CH:31]=[CH:32][CH:33]=3)[CH2:29][O:1][C:2]3[CH:11]=[C:10]4[C:5]([CH2:6][CH2:7][C:8](=[O:38])[NH:9]4)=[CH:4][CH:3]=3)=[N:21]2)=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 19369487HCID 19369487, compoundHCID 19369495HCID 19369495, compound

Product 1

HCID 15411291HCID 15411291, compound

Reagents, catalysts & solvents 1

HCID 74236Tetrabutylammonium BromideCatalyst

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 K2 CO3, 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, recrystallization 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, recrystallization

Sources & evidence

ORD record
ord-7650e23a70c14d15adc0547cc4d1b115
Source dataset
uspto-grants-1998_05
Patent number
US05756518

Reaction notes

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