Butyl bromide → HCID 23471614, compound

HRID 128018Notes

Reaction equation

HRID 128018 reaction equation
[CH3:1][CH:2]1[C:7]([C:8]2[CH:9]=[C:10]3[C:15](=[CH:16][CH:17]=2)[N:14]([CH3:18])[C:13](=[O:19])[CH2:12][C:11]3([CH3:21])[CH3:20])=[N:6][NH:5][C:4](=[O:22])[CH2:3]1.[Na].[CH2:24](Br)[CH2:25][CH2:26][CH3:27]>CN(C)C=O>[CH2:24]([N:5]1[C:4](=[O:22])[CH2:3][CH:2]([CH3:1])[C:7]([C:8]2[CH:9]=[C:10]3[C:15](=[CH:16][CH:17]=2)[N:14]([CH3:18])[C:13](=[O:19])[CH2:12][C:11]3([CH3:21])[CH3:20])=[N:6]1)[CH2:25][CH2:26][CH3:27]

Participants

5

Reactant 3

HCID 8002Butyl bromideHCID 5360545SodiumHCID 23471600HCID 23471600, compound

Product 1

HCID 23471614HCID 23471614, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 6 g of 6-(5-methyl-3-oxo-2,3,4,5-tetrahydropyridazin-6-yl)-1,4,4-trimethyl-1,2,3,4-tetrahydroquinolin-2-one and 60 ml of dimethylformamide was added 1.8 g of sodium hdyride. After 30 minutes, 4.6 g of butyl bromide was added to the mixture and the whole mixture was stirred for one hour. After completion of the reaction, the mixture was poured into ice-cold water and the precipitated crystals were filtered off and recrystallized from a mixture of ethanol and water to give 5.2 g of 6-(2-butyl-5-methyl-3-oxo-2,3,4,5-tetrahydropyridazin-6-yl)-1,4,4-trimethyl-1,2,3,4-tetrahydroquinolin-2-one, melting at 137°-139° C.

Workup

  1. customAfter completion of the reaction
  2. additionthe mixture was poured into ice-cold water
  3. filtrationthe precipitated crystals were filtered off
  4. customrecrystallized from a mixture of ethanol and water

Sources & evidence

ORD record
ord-746b25b0ff0343ab96d3cfe18e29f42f
Source dataset
uspto-grants-1981_03
Patent number
US04258185

Reaction notes

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