N,N-Dimethylaniline → 6-(3-allyl-4-hydroxyphenyl)-4,5-dihydro-3(2H)-pyridazinone

HRID 1579270Notes

Reaction equation

HRID 1579270 reaction equation
C([O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH2:12][CH2:13][C:14](=[O:17])[NH:15][N:16]=2)=[CH:7][CH:6]=1)C=C.CN(C)[C:20]1[CH:25]=CC=C[CH:21]=1>>[CH2:25]([C:10]1[CH:9]=[C:8]([C:11]2[CH2:12][CH2:13][C:14](=[O:17])[NH:15][N:16]=2)[CH:7]=[CH:6][C:5]=1[OH:4])[CH:20]=[CH2:21]

Participants

3

Reactant 2

HCID 949N,N-DimethylanilineHCID 214502236-(4-allyloxyphenyl)-4,5-dihydro-3(2H)-pyridazinone

Product 1

HCID 1355732836-(3-allyl-4-hydroxyphenyl)-4,5-dihydro-3(2H)-pyridazinoneYield 87%

Procedure

A mixture of 6-(4-allyloxyphenyl)-4,5-dihydro-3(2H)-pyridazinone (81.8 g, 0.36 mole) and N,N-dimethylaniline (200 ml) was heated under reflux in an atmosphere of nitrogen for 6 hours, then allowed to cool overnight. The collected product was well washed with ether to give 6-(3-allyl-4-hydroxyphenyl)-4,5-dihydro-3(2H)-pyridazinone (71.5 g, 87%, m.p. 240°-244°C). Recrystallisation from 2-methoxyethanol gave the pure material of m.p. 242°-244°C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux in an atmosphere of nitrogen for 6 hours
  3. temperatureto cool overnight
  4. washThe collected product was well washed with ether

Sources & evidence

ORD record
ord-b3c2f7878c504c94adb535d00562d12c
Source dataset
uspto-grants-1976_01
Patent number
US03931177

Reaction notes

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