3,6-Octanedione → HCID 23275890, compound

HRID 1389998Notes

Reaction equation

HRID 1389998 reaction equation
[NH:1]([C:3]1[N:4]=[N:5][C:6]([N:9]2[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)=[CH:7][CH:8]=1)[NH2:2].[CH3:15][CH2:16][C:17](=O)[CH2:18][CH2:19][C:20](=O)[CH2:21][CH3:22]>C(O)(=O)C>[CH2:21]([C:20]1[N:2]([NH:1][C:3]2[N:4]=[N:5][C:6]([N:9]3[CH2:10][CH2:11][O:12][CH2:13][CH2:14]3)=[CH:7][CH:8]=2)[C:17]([CH2:16][CH3:15])=[CH:18][CH:19]=1)[CH3:22]

Participants

4

Reactant 2

HCID 1650543,6-OctanedioneHCID 12603548HCID 12603548, compound

Product 1

HCID 23275890HCID 23275890, compoundYield 85.7%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Conditions

Temperature
67 °C

Procedure

To 1.95 g (10 m moles) of 3-hydrazino-6-morpholino-pyridazine dissolved in 12 ml of acetic acid, 1.71 g (12 m moles) of 3,6-octanedione dissolved in 4 ml of acetic acid are added at room temperature. The mixture is heated at 67° C. for 2 hours and then evaporated to dryness under vacuum. The oily residue is dissolved in toluene and the solution is evaporated to dryness. The residue is slurried with ice-water and neutralized with sodium bicarbonate to yield 2.58 g of a solid product. Said material, after crystallization from isopropanol gives 1.25 g (42%) of the title product, melting at 186°-9° C. Elemental analysis, I. R., N.M.R. and mass spectra are in agreement with the assigned structure.

Workup

  1. additionare added at room temperature
  2. customevaporated to dryness under vacuum
  3. dissolutionThe oily residue is dissolved in toluene
  4. customthe solution is evaporated to dryness

Sources & evidence

ORD record
ord-2577727d135a48c081c88daa4e556844
Source dataset
uspto-grants-1981_01
Patent number
US04247551

Reaction notes

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