1,3-Benzodioxol-5-ylhydrazine → 3-(2-Benzo[1,3]dioxol-5-yl-2H-pyrazol-3-yl)-1-phenyl-1H-pyridazin-4-one

HRID 1924482Notes

Reaction equation

HRID 1924482 reaction equation
C[N:2](C)/[CH:3]=[CH:4]/[C:5]([C:7]1[C:12](=[O:13])[CH:11]=[CH:10][N:9]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[N:8]=1)=O.[CH2:21]1[O:29][C:28]2[CH:27]=[CH:26][C:25]([NH:30]N)=[CH:24][C:23]=2[O:22]1>C(O)(=O)C>[O:29]1[C:28]2[CH:27]=[CH:26][C:25]([N:30]3[C:5]([C:7]4[C:12](=[O:13])[CH:11]=[CH:10][N:9]([C:14]5[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=5)[N:8]=4)=[CH:4][CH:3]=[N:2]3)=[CH:24][C:23]=2[O:22][CH2:21]1

Participants

4

Reactant 2

HCID 126584411,3-Benzodioxol-5-ylhydrazineHCID 12742246(E)-3-(3-(Dimethylamino)acryloyl)-1-phenylpyridazin-4(1H)-one

Product 1

HCID 462191903-(2-Benzo[1,3]dioxol-5-yl-2H-pyrazol-3-yl)-1-phenyl-1H-pyridazin-4-oneYield 301.7%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

3-((E)-3-Dimethylamino-acryloyl)-1-phenyl-1H-pyridazin-4-one (A-1) (0.2 g; 0.74 mmol) and 3,4-methylenedioxyphenylhydrazine (0.136 g; 0.89 mmol) are dissolved in a sealed tube in acetic acid (4 ml) and irradiated at 180° C. for 10 min. The solvent of the reaction mixture is removed and the crude product is purified by preparative HPLC yielding 0.80 g (30%) of the final product. MS: M=359.0 (M+H)+

Workup

  1. customirradiated at 180° C. for 10 min
  2. customThe solvent of the reaction mixture is removed
  3. customthe crude product is purified by preparative HPLC

Sources & evidence

ORD record
ord-0aa81b4b5aed45cbbecc2bad502ba001
Source dataset
uspto-grants-2012_05
Patent number
US08178538B2

Reaction notes

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