1,3-Cyclohexanedione → Indole

HRID 2047580Notes

Reaction equation

HRID 2047580 reaction equation
C1(=O)CCCC(=O)C1.C1[C:21]2[NH:20][C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:13]=2C(=O)CC1>>[NH:20]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:13]=[CH:21]1

Participants

3

Reactant 2

HCID 104341,3-CyclohexanedioneHCID 9291301,2,3,9-Tetrahydro-4H-carbazol-4-one

Product 1

HCID 798Indole

Conditions

Temperature
25 °C

Procedure

A 0.25 mol/L 1,3-cyclohexanedione/50% sulfuric acid solution was placed in a 200-mL container purged with nitrogen. Then, a 0.25 mol/L phenylhydrazine/50% sulfuric acid solution was added dropwise into the container under stirring at 20000 rpm by CLEARMIX (manufactured by M Technique Co., Ltd.) while the temperature of the liquid in the container was maintained at 25° C. As a result of HPLC analysis, the production rate of 1,2,3,4-tetrahydrocarbazol-4-one was 24% or less.

Workup

  1. custompurged with nitrogen
  2. additionThen, a 0.25 mol/L phenylhydrazine/50% sulfuric acid solution was added dropwise into the container
  3. customAs a result of HPLC analysis

Sources & evidence

ORD record
ord-5caa892205f740fab9be722cc36b6182
Source dataset
uspto-grants-2013_11
Patent number
US08592498B2

Reaction notes

Loading…