2,5-Dimethoxytetrahydrofuran → 6-(4-pyrrol-1-ylphenyl)-4,5-dihydro-2H-pyridazin-3-one

HRID 569771Notes

Reaction equation

HRID 569771 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[CH:10][C:11](=[O:14])[NH:12][N:13]=2)=[CH:4][CH:3]=1.CO[CH:17]1[CH2:21][CH2:20][CH:19](OC)O1>C(O)(=O)C>[N:1]1([C:2]2[CH:7]=[CH:6][C:5]([C:8]3[CH2:9][CH2:10][C:11](=[O:14])[NH:12][N:13]=3)=[CH:4][CH:3]=2)[CH:17]=[CH:21][CH:20]=[CH:19]1

Participants

4

Reactant 2

HCID 790982,5-DimethoxytetrahydrofuranHCID 108670826-(4-aminophenyl)-2H-pyridazin-3-one

Product 1

HCID 201463216-(4-pyrrol-1-ylphenyl)-4,5-dihydro-2H-pyridazin-3-oneYield 25.5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 6-(4-aminophenyl)-3(2H)-pyridazinone (3.7 g) and 2,5-dimethoxytetrahydrofuran (2.6 g) in glacial acetic acid (37 ml) is heated under reflux for four hours. The reaction mixture is cooled, filtered and the solid is washed with ethanol, and finally crystallized from methanol to give 1.2 g of the product, 4,5-dihydro-6-[4-(1H)-pyrrol-1-yl)phenyl]-3(2H)-pyridazinone, mp 222°-223° C.

Workup

  1. temperatureis heated
  2. temperatureunder reflux for four hours
  3. temperatureThe reaction mixture is cooled
  4. filtrationfiltered
  5. washthe solid is washed with ethanol
  6. customfinally crystallized from methanol

Sources & evidence

ORD record
ord-0bfde153d865463e8e0d1d61e8c94efe
Source dataset
uspto-grants-1988_03
Patent number
US04734415

Reaction notes

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