HCID 14209234, compound → HCID 14209219, compound

HRID 1646864Notes

Reaction equation

HRID 1646864 reaction equation
Br[C:2]1[CH:3]=[N:4][C:5]2[C:10]([C:11]=1[NH:12][CH2:13][CH2:14][OH:15])=[CH:9][CH:8]=[CH:7][CH:6]=2.CC(C)([O-])C.[K+]>CN(C)C=O.O>[NH:12]1[C:11]2[C:10]3[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=3[N:4]=[CH:3][C:2]=2[O:15][CH2:14][CH2:13]1

Participants

5

Reactant 2

HCID 14209234HCID 14209234, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 14209219HCID 14209219, compoundYield 23.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 8.0 g of 3-bromo-N-(2-hydroxyethyl)-4-quinolinamine and 4 g of potassium-tert-butoxide in 220 ml of dimethylformamide was heated at reflux for 3 hours. The reaction mixture was cooled to room temperature and diluted with 200 ml of water and the product was extracted with 4 portions of 50 ml of dichloromethane (DCM). The DCM solution was dried over sodium sulfate and concentrated. The oily residue was dissolved in 150 ml of ethanol. To this solution 5 ml of concentrated HCl was added, the HCl salt was separated by filtration and recrystallized from ethanol. This crystalline material was dissolved in 75 ml of water and the solution made alkaline (pH=8) with a sodium bicarbonate solution. The free base was filtered and dried in vacuo to yield 1.3 g of white solid, mp 175°-176° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 3 hours
  3. extractionthe product was extracted with 4 portions of 50 ml of dichloromethane (DCM)
  4. dry with materialThe DCM solution was dried over sodium sulfate
  5. concentrationconcentrated
  6. dissolutionThe oily residue was dissolved in 150 ml of ethanol
  7. additionTo this solution 5 ml of concentrated HCl was added
  8. customthe HCl salt was separated by filtration
  9. customrecrystallized from ethanol
  10. dissolutionThis crystalline material was dissolved in 75 ml of water
  11. filtrationThe free base was filtered
  12. customdried in vacuo

Sources & evidence

ORD record
ord-74fa1593636042f2b1e78778f98cef3a
Source dataset
uspto-grants-1993_01
Patent number
US05182275

Reaction notes

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