1-Propanol, 2-[(3-bromo-7-chloro-4-quinolinyl)amino]- → HCID 14209222, compound

HRID 1252412Notes

Reaction equation

HRID 1252412 reaction equation
Br[C:2]1[CH:3]=[N:4][C:5]2[C:10]([C:11]=1[NH:12][CH:13]([CH3:16])[CH2:14][OH:15])=[CH:9][CH:8]=[C:7]([Cl:17])[CH:6]=2.CC(C)([O-])C.[K+]>CN(C=O)C.O>[Cl:17][C:7]1[CH:8]=[CH:9][C:10]2[C:11]3[NH:12][CH:13]([CH3:16])[CH2:14][O:15][C:2]=3[CH:3]=[N:4][C:5]=2[CH:6]=1

Participants

5

Reactant 2

HCID 142092381-Propanol, 2-[(3-bromo-7-chloro-4-quinolinyl)amino]-HCID 23665647Potassium tert-butoxide

Product 1

HCID 14209222HCID 14209222, compoundYield 33.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 10 g of 3-bromo-7-chloro-N-(2-hydroxy-1-methylethyl)-4-quinolinamine in 28 ml of DMF was stirred and to it was added 4.3 g of potassium-t-butoxide. The mixture was stirred at 120°-140° C. for 2 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 solid 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 215°-217° 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 solid which
  5. customwas purified by HPLC
  6. customRecrystallization from acetone

Sources & evidence

ORD record
ord-369acc1befe845f6a00c266e704388f5
Source dataset
uspto-grants-1988_05
Patent number
US04743601

Reaction notes

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