3,4,5,6-Tetrahydrophthalic anhydride → 2,3,5,6,7,8-Hexahydrophthalazine-1,4-dione

HRID 1383853Notes

Reaction equation

HRID 1383853 reaction equation
[C:1]1(=O)[O:6][C:4](=[O:5])[C:3]2[CH2:7][CH2:8][CH2:9][CH2:10][C:2]1=2.O.O.O.C([O-])(=O)C.[Na+].O.[NH2:21][NH2:22]>C(O)(=O)C>[C:4]1(=[O:5])[C:3]2[CH2:7][CH2:8][CH2:9][CH2:10][C:2]=2[C:1](=[O:6])[NH:22][NH:21]1

Participants

5

Reactant 3

HCID 124753,4,5,6-Tetrahydrophthalic anhydrideHCID 24654Hydrazine hydrate (1:1)HCID 23665404Sodium Acetate Trihydrate

Product 1

HCID 3139202,3,5,6,7,8-Hexahydrophthalazine-1,4-dioneYield 84.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

3,4,5,6-Tetrahydrophthalic anhydride (25 g, 0.164 mol) was dissolved in 40% aqueous acetic acid (500 ml) with sodium acetate trihydrate (26.8 g, 0.197 mol) and hydrazine hydrate (9.58 ml, 0.197 mol). The reaction mixture was heated under reflux overnight and then allowed to cool. The resulting solid was collected by filtration, washed with water and diethyl ether and dried in vacio to give the title-product (23 g, 84%), 1H NMR (250 MHz, d6-DMSO) δ1.64 (4 H, br s, 2 of CH2), 2.34 (4 H, br s, 2 of CH2), 11.30 (2 H, br s, 2 of NH); MS (ES+) m/e 167 [MH]+.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux overnight
  3. temperatureto cool
  4. filtrationThe resulting solid was collected by filtration
  5. washwashed with water and diethyl ether
  6. customdried in vacio

Sources & evidence

ORD record
ord-3ab8041c711143619a8a39377dc50d1f
Source dataset
uspto-grants-2001_07
Patent number
US06255305B1

Reaction notes

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