HCID 14209240, compound → HCID 14209223, compound

HRID 1646869Notes

Reaction equation

HRID 1646869 reaction equation
Br[C:2]1[C:3]([CH3:17])=[N:4][C:5]2[C:10]([C:11]=1[NH:12][CH2:13][CH:14]([OH:16])[CH3:15])=[CH:9][CH:8]=[CH:7][CH:6]=2.CC(C)([O-])C.[K+]>CN(C=O)C>[CH3:15][CH:14]1[O:16][C:2]2[C:3]([CH3:17])=[N:4][C:5]3[CH:6]=[CH:7][CH:8]=[CH:9][C:10]=3[C:11]=2[NH:12][CH2:13]1

Participants

4

Reactant 2

HCID 14209240HCID 14209240, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 14209223HCID 14209223, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 18.5 g of 3-bromo-N-(2-hydroxypropyl)-2-methyl-4-quinolinamine and 7.0 g of potassium tert-butoxide in 100 ml of DMF was stirred at 80°-90° C. for 1 hour. The mixture was cooled to room temperature, diluted with 300 ml of ice-water and stirred for 1 hour, whereupon a solid separated which was filtered and recrystallized twice from isopropanol and finally from isopropyl acetate. The yield was 8.7 g, mp 169°-170° C.

Workup

  1. stirringstirred for 1 hour, whereupon a solid
  2. customseparated which
  3. filtrationwas filtered
  4. customrecrystallized twice from isopropanol and finally from isopropyl acetate

Sources & evidence

ORD record
ord-849845ed353e4fd1a2ac43a1420e9ddd
Source dataset
uspto-grants-1993_01
Patent number
US05182275

Reaction notes

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