Hydrazine → 3-(4-Carbomethoxyphenyl)-6-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)-pyridazine

HRID 1591133Notes

Reaction equation

HRID 1591133 reaction equation
[NH2:1][NH2:2].[C:3]([C:7]1[CH:12]=[CH:11][C:10]([C:13](=O)[CH2:14][CH2:15][C:16]([C:18]2[CH:27]=[CH:26][C:25]3[C:24]([CH3:29])([CH3:28])[CH2:23][CH2:22][C:21]([CH3:31])([CH3:30])[C:20]=3[CH:19]=2)=O)=[CH:9][CH:8]=1)([O:5][CH3:6])=[O:4].[OH-].[Na+]>C(O)C.O>[C:3]([C:7]1[CH:12]=[CH:11][C:10]([C:13]2[N:1]=[N:2][C:16]([C:18]3[CH:27]=[CH:26][C:25]4[C:24]([CH3:29])([CH3:28])[CH2:23][CH2:22][C:21]([CH3:31])([CH3:30])[C:20]=4[CH:19]=3)=[CH:15][CH:14]=2)=[CH:9][CH:8]=1)([O:5][CH3:6])=[O:4]

Participants

6

Reactant 3

HCID 9321HydrazineHCID 14798Sodium HydroxideHCID 147264921-(4-Carbomethoxyphenyl)-4-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)-butane-1,4-dione

Product 1

HCID 147265483-(4-Carbomethoxyphenyl)-6-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)-pyridazine

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

0.3 g (10 millimoles) of 100% pure hydrazine were added dropwise at room temperature to a solution of 4.0 g (10 millimoles) of 1-(4-carbomethoxyphenyl)-4-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)-butane-1,4-dione (for preparation see Example 9) in 50 ml of ethanol. The reaction mixture was then refluxed for 20 minutes, cooled and then stirred into water, and the yellow crystals were filtered off under suction and dried in a stream of nitrogen. For aromatization of unoxidized dihydropyridazine, the crude product was stirred with periodic acid in ethanol until checking by thin layer chromatography showed that mainly a pure product was obtained. The product was then diluted with water, rendered basic with 2N sodium hydroxide solution and extracted with methylene chloride. The organic phase was washed with water, dried over magnesium sulfate and evaporated down. 3.1 g of the title compound remained as an oil; H-NMR (CF3COOH):=8.82 and 8.88 ppm (in each case, d, 2 H, pyridazine-H).

Workup

  1. temperatureThe reaction mixture was then refluxed for 20 minutes
  2. temperaturecooled
  3. filtrationthe yellow crystals were filtered off under suction
  4. customdried in a stream of nitrogen
  5. customwas obtained
  6. extractionextracted with methylene chloride
  7. washThe organic phase was washed with water
  8. dry with materialdried over magnesium sulfate
  9. customevaporated down

Sources & evidence

ORD record
ord-093bf2e8768344d695fbb6f11d9b1b38
Source dataset
uspto-grants-1993_04
Patent number
US05206242

Reaction notes

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