Sulfuric Acid → Indolo(3,2-b)carbazole

HRID 2273513Notes

Reaction equation

HRID 2273513 reaction equation
[CH2:1](C1C2C(=CC=CC=2)NC=1)[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[NH:4][CH:3]=1.S(=O)(=O)(O)O>CO>[CH:9]1[CH:8]=[CH:7][CH:6]=[C:5]2[N:4]=[C:3]3[CH:1]=[C:2]4[C:3](=[N:4][C:5]5[C:10]4=[CH:9][CH:8]=[CH:7][CH:6]=5)[CH:1]=[C:2]3[C:10]=12

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 30713,3'-Diindolylmethane

Product 1

HCID 114764Indolo(3,2-b)carbazoleYield 126.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Under a nitrogen gas stream, about 250.69 g (i.e., about 205.8 mmol) of 3,3′-methylenediindole and about 30.55 g (i.e., about 206.1 mmol) of triethyl orthofomate are dissolved and mixed in methanol within a 3-neck flask. Thereafter, about 5.0 g (i.e., 51.5 mmol) of enriched sulfuric acid is slowly added little by little into the 3-neck flask and then the mixture within the 3-neck flask is refluxed during a single hour. The mixture within the 3-neck flask is frozen to be a normal temperature. Subsequently, about 33 g of indolo(3,2-b)carbazole corresponding to a compound of dark brown is obtained by filtering the frozen mixture.

Workup

  1. temperaturethe mixture within the 3-neck flask is refluxed during a single hour
  2. temperatureThe mixture within the 3-neck flask is frozen

Sources & evidence

ORD record
ord-347090b8281a4b789c4bbf66de2bedb7
Source dataset
uspto-grants-2015_09
Patent number
US09123900B2

Reaction notes

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