Hydrazine hydrate (1:1) → NSC349455

HRID 1719440Notes

Reaction equation

HRID 1719440 reaction equation
[CH3:1][N:2]([CH3:31])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2([C:22]3[CH:27]=[CH:26][C:25]([N:28]([CH3:30])[CH3:29])=[CH:24][CH:23]=3)[C:18]3[C:13](=[CH:14][C:15]([N:19]([CH3:21])[CH3:20])=[CH:16][CH:17]=3)[C:11](=O)O2)=[CH:5][CH:4]=1.[OH2:32].[NH2:33][NH2:34]>C(O)C>[CH3:30][N:28]([CH3:29])[C:25]1[CH:24]=[CH:23][C:22]([C:9]2([C:6]3[CH:5]=[CH:4][C:3]([N:2]([CH3:1])[CH3:31])=[CH:8][CH:7]=3)[C:18]3[C:13](=[CH:14][C:15]([N:19]([CH3:20])[CH3:21])=[CH:16][CH:17]=3)[C:11](=[O:32])[NH:34][NH:33]2)=[CH:27][CH:26]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 73773Crystal Violet lactone

Product 1

HCID 336187NSC349455Yield 80.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

With stirring, a mixture of 1200.0 ml of 80 percent aqueous ethyl alcohol, 25.0 g of 3,3-bis(4-dimethylaminophenyl)-6-dimethylaminophthalide and 35.4 g of 85 percent hydrazine hydrate was maintained at reflux temperature, approximately 90° C., for approximately three hours. After setting overnight at ambient temperature, the resulting slurry was chilled to approximately 5° C. by means of an external ice bath. The solid was collected by filtration, washed four times each with 50.0 ml of cold water and air-dried to obtain 20.8 g of 4,4-bis(4-dimethylaminophenyl)-7-dimethylaminophthalazin-1(2H)-one (Formula III: R=N(CH3)2 ; R1 =R3 =R9 =H; R4 =R5 =R10 =R11 =CH3), a white-colored solid which melted at 265°-270° C. Significant infrared maxima appeared at 1660 cm-1 (C=O;s) and 3400 cm-1 (N-H;m). The nuclear magnetic resonance spectrum was consistent with the assigned structure. Paper treated with an ink formulation of the product produced a blue-green-colored image when traced with an applied voltage stylus.

Workup

  1. temperaturewas maintained
  2. waitAfter setting overnight at ambient temperature
  3. temperaturethe resulting slurry was chilled to approximately 5° C. by means of an external ice bath
  4. filtrationThe solid was collected by filtration
  5. washwashed four times each with 50.0 ml of cold water
  6. customair-dried

Sources & evidence

ORD record
ord-ddd27eae8c474872b6fbbd0ebb39c458
Source dataset
uspto-grants-1985_09
Patent number
US04539579

Reaction notes

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