HCID 14209217, compound → HCID 14209218, compound

HRID 1252415Notes

Reaction equation

HRID 1252415 reaction equation
Br[C:2]1[CH:3]=[N:4][C:5]2[C:10]([C:11]=1[NH:12][CH2:13][CH:14]([OH:16])[CH3:15])=[CH:9][CH:8]=[C:7]([Cl:17])[CH:6]=2.CC(C)([O-])C.[K+]>CN(C)C=O.O>[Cl:17][C:7]1[CH:8]=[CH:9][C:10]2[C:11]3[NH:12][CH2:13][CH:14]([CH3:15])[O:16][C:2]=3[CH:3]=[N:4][C:5]=2[CH:6]=1

Participants

5

Reactant 2

HCID 14209217HCID 14209217, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 14209218HCID 14209218, compoundYield 30.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 11 g of 3-bromo-7-chloro-N-(2-hydroxypropyl)-4-quinolinamine in 33 ml of dimethylformamide was stirred and to it was added 4.3 g of potassium t-butoxide. The mixture was stirred at 130°-140° C. for three hours and then allowed to cool to room temperature. The reaction mixture was diluted with water and the organics were extracted into dichloromethane. Washing with water, drying over anhydrous magnesium sulfate and evaporation of solvents resulted in a crude oil which was purified by HPLC using 2:1 hexane/ethyl acetate as the eluent. Recrystallization from acetone yielded 2.5 g of solid with a melting point of 239°-241° C.

Workup

  1. extractionthe organics were extracted into dichloromethane
  2. washWashing with water
  3. dry with materialdrying over anhydrous magnesium sulfate and evaporation of solvents
  4. customresulted in a crude oil which
  5. customwas purified by HPLC
  6. customRecrystallization from acetone

Sources & evidence

ORD record
ord-3ff8c0a456074e29aaf98f91eb384615
Source dataset
uspto-grants-1988_05
Patent number
US04743601

Reaction notes

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