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Pyridine → 6-[4-(4-ethoxycarbonyl-piperidin-1-yl)-3-nitro-phenyl]-5-methyl-4,5-dihydro-3(2H)-pyridazinone

HRID 1031463
Notes
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Reaction equation

HRID 1031463 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]([CH3:15])[CH2:10][C:11](=[O:14])[NH:12][N:13]=2)=[CH:4][C:3]=1[N+:16]([O-:18])=[O:17].[CH2:19]([O:21][C:22]([CH:24]1[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]1)=[O:23])[CH3:20].N1C=CC=CC=1>O1CCOCC1>[CH2:19]([O:21][C:22]([CH:24]1[CH2:29][CH2:28][N:27]([C:2]2[CH:7]=[CH:6][C:5]([C:8]3[CH:9]([CH3:15])[CH2:10][C:11](=[O:14])[NH:12][N:13]=3)=[CH:4][C:3]=2[N+:16]([O-:18])=[O:17])[CH2:26][CH2:25]1)=[O:23])[CH3:20]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 1049PyridineHCID 70770Ethyl 4-piperidinecarboxylateHCID 28744326-(4-chloro-3-nitrophenyl)-5-methyl-4,5-dihydropyridazin-3(2H)-one

Product 1

HCID 144594706-[4-(4-ethoxycarbonyl-piperidin-1-yl)-3-nitro-phenyl]-5-methyl-4,5-dihydro-3(2H)-pyridazinone

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

2.68 g (10 mmol) of 6-(4-chloro-3-nitro-phenyl)-5-methyl-4,5-dihydro-3(2H)-pyridazinone are boiled under reflux with 3.14 g (20 mmol) of piperidine-4-carboxylic acid ethyl ester and 0.81 ml (10 mmol) of pyridine in 50 ml of dioxane for 5 hours. The reaction mixture is then poured out on 200 ml of ice water and suction filtered to separate the solid, and the filter cake is then washed with water.

Workup

  1. filtrationfiltered
  2. customto separate the solid
  3. washthe filter cake is then washed with water

Sources & evidence

ORD record
ord-4256e1e4cd5f48b586f9e6054528a070
Source dataset
uspto-grants-1990_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04954501

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes