Hydrochloric Acid → 3-(1,4-dioxo-3,4-dihydrophthalazin-2(1H)-yl)propanoic acid

HRID 1723320Notes

Reaction equation

HRID 1723320 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.[O-]CC.[Na+].[C:17]([O:21]CC)(=[O:20])[CH:18]=[CH2:19].Cl>C(O)C.[OH-].[Na+]>[C:17]([CH2:18][CH2:19][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])([OH:21])=[O:20]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8821Ethyl AcrylateHCID 2194012,3-Dihydro-1,4-phthalazinedioneHCID 2723922Sodium ethoxide

Product 1

HCID 9315273-(1,4-dioxo-3,4-dihydrophthalazin-2(1H)-yl)propanoic acidYield 26%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

2,3-Dihydrophthalazine-1,4-dione(8.1 g; 0.05 mol) was suspended in 100 ml of absolute ethanol containing a catalytic amount of sodium ethoxide. Ethyl acrylate (5.0 g; 0.05 mol) was added to the suspension and the mixture was reacted under reflux for 42 hours. The hot reaction mixture was filtered and the solvent removed in vacuo. The product thus formed was dissolved in sodium hydroxide (0.07 M; 250 ml) and stirred overnight. The solution was acidified by the addition of hydrogen chloride resulting in the formation of a white crystalline solid. The solid was recrystallized from water to produce the product, 2-(2'-carboxyethyl)-2,3-dihydrophthalazine-1,4-dione.

Workup

  1. customthe mixture was reacted
  2. temperatureunder reflux for 42 hours
  3. filtrationThe hot reaction mixture was filtered
  4. customthe solvent removed in vacuo
  5. customThe product thus formed
  6. customThe solid was recrystallized from water

Sources & evidence

ORD record
ord-062da18124974c3ebe7c6aafee82c926
Source dataset
uspto-grants-1989_08
Patent number
US04861778

Reaction notes

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