1-Piperazinecarboxylic acid, ethyl ester → 6-[4-(4-ethoxycarbonyl-piperazin-1-yl)-3-nitro-phenyl]-4,5-dihydro-5-methyl-3(2H)-pyridazinone

HRID 1031458Notes

Reaction equation

HRID 1031458 reaction equation
[CH2:1]([O:3][C:4]([N:6]1[CH2:11][CH2:10][NH:9][CH2:8][CH2:7]1)=[O:5])[CH3:2].Cl[C:13]1[CH:18]=[CH:17][C:16]([C:19]2[CH:20]([CH3:26])[CH2:21][C:22](=[O:25])[NH:23][N:24]=2)=[CH:15][C:14]=1[N+:27]([O-:29])=[O:28]>CN(C)C=O>[CH2:1]([O:3][C:4]([N:6]1[CH2:7][CH2:8][N:9]([C:13]2[CH:18]=[CH:17][C:16]([C:19]3[CH:20]([CH3:26])[CH2:21][C:22](=[O:25])[NH:23][N:24]=3)=[CH:15][C:14]=2[N+:27]([O-:29])=[O:28])[CH2:10][CH2:11]1)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 84311-Piperazinecarboxylic acid, ethyl esterHCID 28744326-(4-chloro-3-nitrophenyl)-5-methyl-4,5-dihydropyridazin-3(2H)-one

Product 1

HCID 144594626-[4-(4-ethoxycarbonyl-piperazin-1-yl)-3-nitro-phenyl]-4,5-dihydro-5-methyl-3(2H)-pyridazinoneYield 76.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

24.5 ml (168 mmol) of 1-ethoxycarbonylpiperazine are added to a solution of 15.0 g (56 mmol) of 6-(4-chloro-3-nitro-phenyl)-4,5-dihydro-5-methyl-3(2H)-pyridazinone in 50 ml of dimethyl formamide and the solution is stirred at a reaction temperature of 100° C. for 3 hours. When the reaction mixture is cold, it is poured out on 300 ml of ice water with vigorous stirring. The precipitated solid is suction filtered, washed with a small quantity of ethanol and diethyl ether and recrystallized from 500 ml of ethanol. 16.7 g (76%) of orange yellow crystals, m.p. 140° to 142° C., are obtained.

Workup

  1. filtrationfiltered
  2. washwashed with a small quantity of ethanol and diethyl ether
  3. customrecrystallized from 500 ml of ethanol

Sources & evidence

ORD record
ord-71bb36824dad4bac9481fd977d6a916e
Source dataset
uspto-grants-1990_09
Patent number
US04954501

Reaction notes

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