4-Hydrazinobenzoic acid → HCID 19966842, compound

HRID 976239Notes

Reaction equation

HRID 976239 reaction equation
[C:1]1(=[O:18])[N:5]([CH:6]2[CH2:11][CH2:10][C:9](=O)[CH2:8][CH2:7]2)[C:4](=[O:13])[C:3]2=[CH:14][CH:15]=[CH:16][CH:17]=[C:2]12.[NH:19]([C:21]1[CH:29]=[CH:28][C:24]([C:25]([OH:27])=[O:26])=[CH:23][CH:22]=1)N>C(O)(=O)C>[C:25]([C:24]1[CH:23]=[C:22]2[C:21](=[CH:29][CH:28]=1)[NH:19][C:9]1[CH2:10][CH2:11][CH:6]([N:5]3[C:4](=[O:13])[C:3]4=[CH:14][CH:15]=[CH:16][CH:17]=[C:2]4[C:1]3=[O:18])[CH2:7][C:8]2=1)([OH:27])=[O:26]

Participants

4

Reactant 2

HCID 120894-Hydrazinobenzoic acidHCID 119983912-(4-oxocyclohexyl)-2,3-dihydro-1H-isoindole-1,3-dione

Product 1

HCID 19966842HCID 19966842, compoundYield 41.7%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 4-phthalimidocyclohexanone (2.43 g) and 4-hydrazinobenzoic acid (1.52 g) were combined in acetic acid and boiled for 12 hours. The precipitate was filtered and washed with acetic acid (3×10 ml) and diethyl ether (3×10 ml) to give 6-carboxy-3-phthalimido-1,2,3,4-tetrahydrocarbazole (1.50 g) m.p. 345°-348° C.

Workup

  1. filtrationThe precipitate was filtered
  2. washwashed with acetic acid (3×10 ml) and diethyl ether (3×10 ml)

Sources & evidence

ORD record
ord-eeac47f1578a4a4e9276c2a2546b3182
Source dataset
uspto-grants-1997_03
Patent number
US05612331

Reaction notes

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