Toluene → HCID 20268301, compound

HRID 1719442Notes

Reaction equation

HRID 1719442 reaction equation
C(N1[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][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH3:46])[C:25]=3[CH3:47])[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:16](=O)O2)=[C:6]1[CH3:48])CCC.[OH2:49].[NH2:50][NH2:51].C(OCCO)C.[OH-].[NH4+:59].[Cl-].[Na+].[C:62]1(C)[CH:67]=CC=[CH:64][CH:63]=1>>[CH2:67]([N:59]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][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH3:46])[C:25]=3[CH3:47])[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:16](=[O:49])[NH:51][NH:50]2)=[C:6]1[CH3:48])[CH2:62][CH2:63][CH3:64]

Participants

7

Reactant 6

HCID 1140TolueneHCID 5234Sodium ChlorideHCID 8076Glycol monoethyl etherHCID 14923Ammonium HydroxideHCID 24654Hydrazine hydrate (1:1)HCID 20268297HCID 20268297, compound

Product 1

HCID 20268301HCID 20268301, compound

Conditions

Temperature
100 °C

Procedure

With stirring a mixture of 10.0 g of 3-(1-butyl-2-methylindol-3-yl)-3-(1-tetradecyl-2-methylindol-3-yl)phthalide, 9.4 g of 85 percent hydrazine hydrate and 50.0 ml of 2-ethoxyethanol was maintained at approximately 100° C. for approximately two hours. After cooling the reaction mixture to approximately 50° C., there was added slowly 75.0 ml of 5 percent aqueous ammonium hydroxide and 75.0 ml of toluene and a small portion of saturated sodium chloride solution. The water layer was separated and extracted a second time with 75.0 ml of fresh toluene. The two toluene portions were combined, washed with saturated sodium chloride solution, and dried over anhydrous sodium sulfate. The dried toluene layer was then concentrated under vacuum to obtain 11.5 g of 4-(1-butyl-2-methylindol-3-yl)-4-(1-tetradecyl-2-methylindol-3-yl)phthalazin-1(2H)-one (Formula V: R=R1 =R8 =R14 =H; R6 =C4H9 ; R7 =R13 =CH3 ; R12 =C14H29), a thick dark brown oil which upon standing turned into a wax-like solid. A significant infrared maximum appeared at 1668 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 magenta-colored image when traced with an applied voltage stylus.

Workup

  1. temperatureAfter cooling the reaction mixture to approximately 50° C.
  2. customThe water layer was separated
  3. extractionextracted a second time with 75.0 ml of fresh toluene
  4. washwashed with saturated sodium chloride solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationThe dried toluene layer was then concentrated under vacuum

Sources & evidence

ORD record
ord-b90d64754f3b4a6885ff24e5773fb585
Source dataset
uspto-grants-1985_09
Patent number
US04539579

Reaction notes

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