Cyclooctanone → HCID 13533647, compound

HRID 464142Notes

Reaction equation

HRID 464142 reaction equation
Cl.[N+:2]([C:5]1[CH:6]=[C:7]([NH:11]N)[CH:8]=[CH:9][CH:10]=1)([O-:4])=[O:3].[C:13]1(=O)[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1>C(O)(=O)C>[N+:2]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:6]=1[C:13]1[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][C:14]=1[NH:11]2)([O-:4])=[O:3]

Participants

4

Reactant 2

HCID 10403CyclooctanoneHCID 54642853-Nitrophenylhydrazinium(1+) chloride

Product 1

HCID 13533647HCID 13533647, compoundYield 32.7%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

3-Nitrophenylhydrazine hydrochloride (50 g, 0.26 mol) and cyclooctanone (32.2 g, 0.25 mol) were refluxed in 400 mL of glacial acetic acid for 6 hours. The solution was allowed to cool and the separated solid was filtered, washed with water and recrystallized from absolute ethanol to afford 20 g (31% yield) of 6,7,8,9,10,11-hexahydro-1-nitro-5H-cyclooct[b]indole; m.p. 189°-191° C.

Workup

  1. temperatureto cool
  2. filtrationthe separated solid was filtered
  3. washwashed with water
  4. customrecrystallized from absolute ethanol

Sources & evidence

ORD record
ord-c17099a59953413da414c06e3f5a59b5
Source dataset
uspto-grants-1985_10
Patent number
US04546193

Reaction notes

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