Methylhydrazine → Trans-6-[2-(4-Hydroxyphenyl)ethenyl]-2-methyl-1(2H)-phthalazinone

HRID 978663Notes

Reaction equation

HRID 978663 reaction equation
O[CH:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9](/[CH:12]=[CH:13]/[C:14]3[CH:19]=[CH:18][C:17]([O:20]C)=[CH:16][CH:15]=3)[CH:10]=2)[C:4](=O)[O:3]1.[CH3:22][NH:23][NH2:24]>C(O)C>[OH:20][C:17]1[CH:18]=[CH:19][C:14](/[CH:13]=[CH:12]/[C:9]2[CH:10]=[C:11]3[C:6](=[CH:7][CH:8]=2)[C:4](=[O:3])[N:23]([CH3:22])[N:24]=[CH:2]3)=[CH:15][CH:16]=1

Participants

4

Reactant 2

HCID 6061MethylhydrazineHCID 13827310Trans-3-Hydroxy-5-[2-(4-methoxyphenyl)ethenyl]phthalide

Product 1

HCID 13827297Trans-6-[2-(4-Hydroxyphenyl)ethenyl]-2-methyl-1(2H)-phthalazinone

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Trans-3-Hydroxy-5-[2-(4-methoxyphenyl)ethenyl]phthalide (15 g) was dissolved in refluxing ethanol (85 ml) and methylhydrazine (10 ml) was added slowly. The resulting suspension was refluxed for 3 hours, then cooled and filtered to give the 2-methyl-1(2H)-phthalazinone, mp 223°-225° C. The methoxy phthalazinone (10 g) was mixed with pyridine hydrochloride (35 g) and heated to 180° C. for 10 hours. The mixture was diluted with water, filtered and washed with isopropanol to give the desired phenol (4.3 g), mp 282°-284° C.

Workup

  1. additionwas added slowly
  2. temperatureThe resulting suspension was refluxed for 3 hours
  3. temperaturecooled
  4. filtrationfiltered

Sources & evidence

ORD record
ord-53e16e1587dc4636b61590cc284dbf8c
Source dataset
uspto-grants-1987_05
Patent number
US04665181

Reaction notes

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