Acetic Acid → 1-Propanol, 2-[(3-bromo-7-chloro-4-quinolinyl)amino]-

HRID 2165838Notes

Reaction equation

HRID 2165838 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([NH:12][CH:13]([CH3:16])[CH2:14][OH:15])=[CH:7][CH:8]=[N:9]2)=[CH:4][CH:3]=1.C(O)(=O)C.[Br:21]Br>O.[OH-].[Na+]>[Br:21][C:7]1[CH:8]=[N:9][C:10]2[C:5]([C:6]=1[NH:12][CH:13]([CH3:16])[CH2:14][OH:15])=[CH:4][CH:3]=[C:2]([Cl:1])[CH:11]=2

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 24408BromineHCID 14209229HCID 14209229, compound

Product 1

HCID 142092381-Propanol, 2-[(3-bromo-7-chloro-4-quinolinyl)amino]-Yield 57%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 14798Sodium HydroxideSolvent

Procedure

A mixture of 12 g of 7-chloro-N-(2-hydroxy-1-methylethyl)4-quinolinamine and 112 ml of acetic acid was stirred at room temperature and to it 8 g of bromine was added dropwise over a thirty minute period. The product precipitated from the solution as the hydrobromide salt and it was isolated by filtration, dissolved in water and basified with sodium hydroxide. The free base was extracted into dichloromethane and evaporation of solvents resulted in a solid which was purified by HPLC using 95:5 dichloromethane/methanol as the eluent. Recrystallization from isopropanol yielded 9 g of crystalline solid with a melting point of 145°-147° C.

Workup

  1. additionwas added dropwise over a thirty minute period
  2. customThe product precipitated from the solution as the hydrobromide salt
  3. customit was isolated by filtration
  4. extractionThe free base was extracted into dichloromethane and evaporation of solvents
  5. customresulted in a solid which
  6. customwas purified by HPLC
  7. customRecrystallization from isopropanol

Sources & evidence

ORD record
ord-77ff1e0ffe3a44a7a5af0312ba70533f
Source dataset
uspto-grants-1990_07
Patent number
US04942168

Reaction notes

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