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

HRID 596680Notes

Reaction equation

HRID 596680 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 (81.8g, 0.36mole; 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 (71.5g, 87%, m.p. 240°-244° C). Recrystallisation from 2-methoxyethanol gave the pure material of m.p. 242°-244° C. (Found: C, 67.54; H, 6.20; N, 12.04; M+, 230. C13H14N2O2 requires: C, 67.81; H, 6.13; N, 12.17%, M, 230).

Workup

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

Sources & evidence

ORD record
ord-f0eb764ed6b545289553472eb29db011
Source dataset
uspto-grants-1977_03
Patent number
US04011321

Reaction notes

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