Ethanol → HCID 20268298, compound

HRID 1719441Notes

Reaction equation

HRID 1719441 reaction equation
[CH2:1]([N:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]([C:14]2([C:24]3[C:32]4[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=4)[N:26]([CH2:33][CH2:34][CH2:35][CH3:36])[C:25]=3[CH3:37])[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:16](=[O:17])O2)=[C:6]1[CH3:38])[CH2:2][CH2:3][CH3:4].C(O)C.O.[NH2:43][NH2:44]>O>[CH2:1]([N:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]([C:14]2([C:24]3[C:32]4[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=4)[N:26]([CH2:33][CH2:34][CH2:35][CH3:36])[C:25]=3[CH3:37])[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:16](=[O:17])[NH:44][NH:43]2)=[C:6]1[CH3:38])[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 702EthanolHCID 24654Hydrazine hydrate (1:1)HCID 1625831(3H)-Isobenzofuranone, 3,3-bis(1-butyl-2-methyl-1H-indol-3-yl)-

Product 1

HCID 20268298HCID 20268298, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

With stirring, a mixture of 25.0 g of 3,3-bis(1-butyl-2-methylindol-3-yl)phthalide, 800.0 ml of ethyl alcohol, 200.0 ml of water and 29.4 g of 85 percent hydrazine hydrate was maintained at reflux temperature for approximately forty-eight hours. The resulting mixture was chilled in an external ice bath to a temperature in the range of 0°-5° C. The solid was collected by filtration, washed with chilled ethyl alcohol and dried in an air oven to obtain 23.65 g of 4,4-bis(1-butyl-2-methylindol-3-yl)-phthalazin-1(2H)-one (Formula V: R=R1 =R8 =R14 =H; R6 =R12 =C4H9 ; R7 =R13 =CH3), a pale orange-colored solid which melted at 205.5°-206.5° C. In the infrared spectrum maxima appeared at 3400 cm-1 (N-H;w) and 1670 cm-1 (C=O;s). The nuclear magnetic resonance spectrum was consistent with the assigned structure. Paper treated with an ink formulation of the product produced a purple-colored image when traced with an applied voltage stylus.

Workup

  1. temperaturewas maintained
  2. temperatureat reflux temperature for approximately forty-eight hours
  3. temperatureThe resulting mixture was chilled in an external ice bath to a temperature in the range of 0°-5° C
  4. filtrationThe solid was collected by filtration
  5. washwashed with chilled ethyl alcohol
  6. customdried in an air oven

Sources & evidence

ORD record
ord-7eb14d721d5a41cb8f083a0b9de79c48
Source dataset
uspto-grants-1985_09
Patent number
US04539579

Reaction notes

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