Acetic Acid → 6-[4-(2,4-Dihydroxyphenyl)methyleneaminophenyl]-4,5-dihydropyridazin-3(2H)one

HRID 1886316Notes

Reaction equation

HRID 1886316 reaction equation
[OH:1][C:2]1[CH:9]=[C:8]([OH:10])[CH:7]=[CH:6][C:3]=1[CH:4]=O.[NH2:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[CH2:19][CH2:20][C:21](=[O:24])[NH:22][N:23]=2)=[CH:14][CH:13]=1.C(O)(=O)C>C(O)C.CN(C=O)C>[OH:1][C:2]1[CH:9]=[C:8]([OH:10])[CH:7]=[CH:6][C:3]=1[CH:4]=[N:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[CH2:19][CH2:20][C:21](=[O:24])[NH:22][N:23]=2)=[CH:14][CH:13]=1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 72132,4-DihydroxybenzaldehydeHCID 6767506-(4-Aminophenyl)-4,5-dihydropyridazin-3(2H)-one

Product 1

HCID 1357087766-[4-(2,4-Dihydroxyphenyl)methyleneaminophenyl]-4,5-dihydropyridazin-3(2H)one

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6228DimethylformamideSolvent

Procedure

A solution containing 0.42 g (0.003 mol) of 2,4-dihydroxybenzaldehyde, 0.57 g (0.003 mol) of 6-(4-aminophenyl)-4,5-dihydropyridazin-3(2H)one and 0.05 ml of acetic acid in a mixture of 40 ml of ethanol and 20 ml of DMF was refluxed for 4 h. After cooling the product was filtered and washed with ethanol. Yield 0.80 g (85%), m.p. 350° C. (decomp).

Workup

  1. temperaturewas refluxed for 4 h
  2. temperatureAfter cooling the product
  3. filtrationwas filtered
  4. washwashed with ethanol

Sources & evidence

ORD record
ord-cf15a93283e6414b8045425a7487c88a
Source dataset
uspto-grants-1992_09
Patent number
US05151420

Reaction notes

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