Dimethylformamide → 2-carbopropoxy-6-(3-(quinolin-2-ylmethoxy)benzyloxy)-4-oxo-4H1-benzopyran

HRID 1110900Notes

Reaction equation

HRID 1110900 reaction equation
Cl[CH2:2][C:3]1[CH:4]=[C:5]([CH:18]=[CH:19][CH:20]=1)[O:6][CH2:7][C:8]1[CH:17]=[CH:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:9]=1.[C:21]([C:27]1[O:28][C:29]2[CH:37]=[CH:36][C:35]([OH:38])=[CH:34][C:30]=2[C:31](=[O:33])[CH:32]=1)([O:23][CH2:24][CH2:25][CH3:26])=[O:22].C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>CC(C)=O>[C:21]([C:27]1[O:28][C:29]2[CH:37]=[CH:36][C:35]([O:38][CH2:2][C:3]3[CH:20]=[CH:19][CH:18]=[C:5]([O:6][CH2:7][C:8]4[CH:17]=[CH:16][C:15]5[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=5)[N:9]=4)[CH:4]=3)=[CH:34][C:30]=2[C:31](=[O:33])[CH:32]=1)([O:23][CH2:24][CH2:25][CH3:26])=[O:22]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 145017062-(3-Chloromethylphenoxy)methylquinolineHCID 199138472-carbopropoxy-6-hydroxy-4-oxo-4H-1-benzopyran

Product 1

HCID 199138482-carbopropoxy-6-(3-(quinolin-2-ylmethoxy)benzyloxy)-4-oxo-4H1-benzopyranYield 28.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 3.47 g of 2-((3-chloromethylphenoxy)methyl)-quinoline, 3.04 g of 2-carbopropoxy-6-hydroxy-4-oxo-4H-1-benzopyran, 1.69 g of potassium carbonate and 1 ml of dimethylformamide is refluxed in 50 ml of acetone for 41 hours. The mixture is concentrated in vacuo and the residue is dissolved in water. This solution is neutralized with diluted hydrochloric acid and the resulting solid is filtered off and purified by flash silica gel chromatography in propanol-dimethylformamide to give 1.71 g of 2-carbopropoxy-6-(3-(quinolin-2-ylmethoxy)benzyloxy)-4-oxo-4H1-benzopyran as a white solid having an m.p. of 109°-10° C.

Workup

  1. concentrationThe mixture is concentrated in vacuo
  2. dissolutionthe residue is dissolved in water
  3. filtrationthe resulting solid is filtered off
  4. custompurified by flash silica gel chromatography in propanol-dimethylformamide

Sources & evidence

ORD record
ord-a384514d2a9c4a9cb5559644055ee6e8
Source dataset
uspto-grants-1990_12
Patent number
US04977162

Reaction notes

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