Methyl vinyl ketone → 3-(3-oxobutyl)-2H-phthalazine-1,4-dione

HRID 1723322Notes

Reaction equation

HRID 1723322 reaction equation
[C:1]1(=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[NH:3][NH:2]1.[CH:13]([C:15]([CH3:17])=[O:16])=[CH2:14]>C(O)C>[O:16]=[C:15]([CH3:17])[CH2:13][CH2:14][N:3]1[NH:2][C:1](=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]1=[O:11]

Participants

4

Reactant 2

HCID 6570Methyl vinyl ketoneHCID 2194012,3-Dihydro-1,4-phthalazinedione

Product 1

HCID 2423013-(3-oxobutyl)-2H-phthalazine-1,4-dione

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2,3-Dihydrophthalazine-1,4-dione (16.2 g; 0.1 mol) was suspended in 95 percent ethanol (200 ml). The suspension was heated to reflux and methyl vinyl ketone (8.4 g; 0.12 mol) was added to the refluxing suspension. With the ketone in the reaction mixture, the mixture was refluxed for 41 hours. The solid remaining after refluxing was filtered. The filtrate was concentrated to obtain the product which was crystallized from ethanol. The yield was determined to be 80 percent. The product had a melting point of 152°-153° C.

Workup

  1. temperatureThe suspension was heated
  2. temperatureto reflux
  3. temperatureafter refluxing
  4. filtrationwas filtered
  5. concentrationThe filtrate was concentrated
  6. customto obtain the product which
  7. customwas crystallized from ethanol

Sources & evidence

ORD record
ord-ab1b8c7343bd4979934d175de40f466d
Source dataset
uspto-grants-1989_08
Patent number
US04861778

Reaction notes

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