Bromine → 3-Bromo-N-(2,3-dihydroxypropyl)-2-methyl-4-quinolinamine

HRID 2165842Notes

Reaction equation

HRID 2165842 reaction equation
[Br:1]Br.[OH:3][CH:4]([CH2:18][OH:19])[CH2:5][NH:6][C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]=[C:9]([CH3:17])[CH:8]=1>C(O)(=O)C>[Br:1][C:8]1[C:9]([CH3:17])=[N:10][C:11]2[C:16]([C:7]=1[NH:6][CH2:5][CH:4]([OH:3])[CH2:18][OH:19])=[CH:15][CH:14]=[CH:13][CH:12]=2

Participants

4

Reactant 2

HCID 24408BromineHCID 142092313-[(2-Methylquinolin-4-yl)amino]propane-1,2-diol

Product 1

HCID 142092413-Bromo-N-(2,3-dihydroxypropyl)-2-methyl-4-quinolinamine

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Bromine (33.7 g) was added dropwise to a solution of 49 g of N-(2,3-dihydroxypropyl)-2-methyl-4-quinolinamine in 600 ml of acetic acid. After two hours of stirring, the resultant oil was separated by decantation, dissolved in 500 ml of water and the mixture made alkaline (pH=10) with potassium carbonate. The resultant free base solid was filtered and recrystallized from ethanol. The yield was 33 g, mp 140°-141° C.

Workup

  1. customthe resultant oil was separated by decantation
  2. dissolutiondissolved in 500 ml of water
  3. filtrationThe resultant free base solid was filtered
  4. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-83eb8e73895b40bc8841848be1bc6e8c
Source dataset
uspto-grants-1990_07
Patent number
US04942168

Reaction notes

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