Chloroform → HCID 10790513, compound

HRID 324026Notes

Reaction equation

HRID 324026 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([CH:8]2[C:17]3[C:12](=[CH:13][C:14]([OH:20])=[C:15]([O:18][CH3:19])[CH:16]=3)[CH:11]=[CH:10][C:9]2(C(OC)=O)[C:21]([O:23][CH3:24])=[O:22])[CH:5]=[CH:4][N:3]=1.[H-].[Na+].[CH:31]1(Br)[CH2:35][CH2:34][CH2:33][CH2:32]1.C(Cl)(Cl)Cl>CN(C)C=O.O>[Cl:1][C:2]1[CH:7]=[C:6]([C:8]2[C:17]3[C:12](=[CH:13][C:14]([O:20][CH:31]4[CH2:35][CH2:34][CH2:33][CH2:32]4)=[C:15]([O:18][CH3:19])[CH:16]=3)[CH:11]=[C:10]([C:21]([O:23][CH3:24])=[O:22])[C:9]=2[C:21]([O:23][CH3:24])=[O:22])[CH:5]=[CH:4][N:3]=1

Participants

7

Reactant 4

HCID 6212ChloroformHCID 8728BromocyclopentaneHCID 24758Sodium hydrideHCID 22007341HCID 22007341, compound

Product 1

HCID 10790513HCID 10790513, compoundYield 32%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-(2-chloro-4-pyridyl)-2,2-bis(methoxycarbonyl)-6-hydroxy-7-methoxynaphthalene (3.34 g) in dimethylformamide (150 ml) is added sodium hydride (0.4 g) under ice-cooling, and the mixture is stirred at room temperature for 30 minutes. To the reaction mixture is added dropwise cyclopentyl bromide (1.8 ml), and the mixture is heated with stirring at 80° C. overnight. The mixture is heated at 130° C. for two hours. To the resultant are added chloroform and water, and the chloroform layer is separated, washed, dried, and concentrated under reduced pressure to remove the solvent. The residue is crystallized from 1-(2-chloro-4-pyridyl)-2,3-bis(methoxycarbonyl)-6-cyclopentyloxy-7-methoxynaphthalene (1.24 g, yield; 32%).

Workup

  1. temperaturecooling
  2. temperaturethe mixture is heated
  3. stirringwith stirring at 80° C. overnight
  4. temperatureThe mixture is heated at 130° C. for two hours
  5. customthe chloroform layer is separated
  6. washwashed
  7. customdried
  8. concentrationconcentrated under reduced pressure
  9. customto remove the solvent

Sources & evidence

ORD record
ord-513c2b67bcab47f5a8c519b24232d0bb
Source dataset
uspto-grants-2001_04
Patent number
US06214996B1

Reaction notes

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