Sodium Carbonate → 3,4-dihydro-8-methyl-6-(1-piperazinyl)-2(1H)-quinolinone hydrobromide

HRID 704620Notes

Reaction equation

HRID 704620 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([CH3:12])[CH:11]=1)[NH:8][C:7](=[O:13])[CH2:6][CH2:5]2.Br.[Br:15][CH2:16][CH2:17][NH:18][CH2:19][CH2:20]Br.C(=O)([O-])[O-].[Na+].[Na+]>CO>[BrH:15].[CH3:12][C:10]1[CH:11]=[C:2]([N:1]2[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]2)[CH:3]=[C:4]2[C:9]=1[NH:8][C:7](=[O:13])[CH2:6][CH2:5]2

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 12692731Ethanamine, 2-bromo-N-(2-bromoethyl)-, hydrobromide (1:1)HCID 146275496-Amino-8-methyl-3,4-dihydroquinolin-2(1H)-one

Product 1

HCID 200728683,4-dihydro-8-methyl-6-(1-piperazinyl)-2(1H)-quinolinone hydrobromideYield 60.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
64 °C

Procedure

A mixture of 6-amino-8-methyl-3,4-dihydro-2(1H)-quinolinone (19.4 g), bis(2-bromoethyl)amine hydrobromide (41 g) and methanol (140 ml) was stirred for 13 hours at 64° C. After cooling, sodium carbonate (5.83 g) was added thereto and the mixture was stirred for 9 hours at 70° C. After cooling, the resulting precipitate was collected by filtration and the residue was washed with methanol to give 3,4-dihydro-8-methyl-6-(1-piperazinyl)-2(1H)-quinolinone hydrobromide (21.6 g).

Workup

  1. temperatureAfter cooling
  2. stirringthe mixture was stirred for 9 hours at 70° C
  3. temperatureAfter cooling
  4. filtrationthe resulting precipitate was collected by filtration
  5. washthe residue was washed with methanol

Sources & evidence

ORD record
ord-217e611015d54f56bbe1fca582973d06
Source dataset
uspto-grants-1991_01
Patent number
US04988698

Reaction notes

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