Bromine → HCID 14209240, compound

HRID 2165840Notes

Reaction equation

HRID 2165840 reaction equation
[Br:1]Br.[OH:3][CH:4]([CH3:18])[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])[CH3:18])=[CH:15][CH:14]=[CH:13][CH:12]=2

Participants

4

Reactant 2

HCID 24408BromineHCID 198000332-Propanol, 1-[(2-methyl-4-quinolinyl)amino]-

Product 1

HCID 14209240HCID 14209240, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Bromine (32 g) was added dropwise to a solution of 44 g of N-(2-hydroxypropyl)-2-methyl-4-quinolinamine in 600 ml of acetic acid. The solution was stirred for 1 hour and the HBr salt was filtered and washed with a small amount of acetic acid. It was then dissolved in 500 ml of water and an aqueous KOH solution was added, whereupon the free base precipitated. It was filtered and recrystallized from isopropanol. The yield was 22 g, mp 147°-149° C.

Workup

  1. filtrationthe HBr salt was filtered
  2. washwashed with a small amount of acetic acid
  3. dissolutionIt was then dissolved in 500 ml of water
  4. additionan aqueous KOH solution was added, whereupon the free base
  5. customprecipitated
  6. filtrationIt was filtered
  7. customrecrystallized from isopropanol

Sources & evidence

ORD record
ord-fd37a30b42f148938c2c1c5574dc176b
Source dataset
uspto-grants-1990_07
Patent number
US04942168

Reaction notes

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