4-Methoxyphenylhydrazine hydrochloride → 3-Phthalimido-6-methoxy-1,2,3,4-tetrahydrocarbazole

HRID 128750

Reaction equation

HRID 128750 reaction equation
Cl.[CH3:2][O:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10]N)=[CH:6][CH:5]=1.[C:12]1(=[O:29])[N:16]([CH:17]2[CH2:22][CH2:21][C:20](=O)[CH2:19][CH2:18]2)[C:15](=[O:24])[C:14]2=[CH:25][CH:26]=[CH:27][CH:28]=[C:13]12>C(O)C>[C:15]1(=[O:24])[N:16]([CH:17]2[CH2:18][C:19]3[C:8]4[C:7](=[CH:6][CH:5]=[C:4]([O:3][CH3:2])[CH:9]=4)[NH:10][C:20]=3[CH2:21][CH2:22]2)[C:12](=[O:29])[C:13]2=[CH:28][CH:27]=[CH:26][CH:25]=[C:14]12

Participants

4

Reactant 2

HCID 27239044-Methoxyphenylhydrazine hydrochlorideHCID 119983912-(4-oxocyclohexyl)-2,3-dihydro-1H-isoindole-1,3-dione

Product 1

HCID 108075243-Phthalimido-6-methoxy-1,2,3,4-tetrahydrocarbazoleYield 93.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Reaction of 4-methoxyphenyl hydrazine hydrochloride (0.87 g, 5.0 mmol) with 4-phthalimido-cyclohexanone (1.22 g, 5.0 mmol) in ethanol (20 ml) heated under reflux for 2 hr, followed by cooling and removal of the precipitated solid by filtration gave 3-phthalimido-6-methoxy-1,2,3,4-tetrahydrocarbazole (1.62 g).

Workup

  1. temperatureheated
  2. temperatureunder reflux for 2 hr
  3. temperatureby cooling
  4. customremoval of the precipitated solid
  5. filtrationby filtration

Sources & evidence

ORD record
ord-2fe2b57280cf4d178a630ea8ac6bf48e
Source dataset
uspto-grants-1995_11
Patent number
US05464864

Linked notes

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