2-Aminoquinoline → HCID 13589568, compound

HRID 653058Notes

Reaction equation

HRID 653058 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.Br[CH2:13][C:14]([C:16]1[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=1)=O.C(=O)(O)[O-].[Na+]>C(O)CC>[Cl:22][C:19]1[CH:20]=[CH:21][C:16]([C:14]2[N:1]=[C:2]3[CH:11]=[CH:10][C:9]4[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=4)[N:3]3[CH:13]=2)=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 113792-AminoquinolineHCID 68303p-Chlorophenacyl bromideHCID 516892Sodium Bicarbonate

Product 1

HCID 13589568HCID 13589568, compound

Reagents, catalysts & solvents 1

HCID 10311-PropanolSolvent

Procedure

17.7 g (0.123 mole) of 2-aminoquinoline, 28.7 g (1 equivalent of α-bromo-p-chloroacetophenone and 20.6 g (2 equivalents) of sodium bicarbonate are mixed in 180 ml of n-propanol and heated under reflux for 20 hours. The precipitate obtained is filtered off, washed with ethanol and water and dried. A white solid is obtained which is recrystallized from nitromethane.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 20 hours
  3. customThe precipitate obtained
  4. filtrationis filtered off
  5. washwashed with ethanol and water
  6. customdried
  7. customA white solid is obtained which
  8. customis recrystallized from nitromethane

Sources & evidence

ORD record
ord-63135ecdd206441185ac69026cb63ccb
Source dataset
uspto-grants-1987_06
Patent number
US04675323

Reaction notes

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