3,3,-Diindolylmethane → Indolo(3,2-b)carbazole

HRID 558041Notes

Reaction equation

HRID 558041 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.C(O[CH2:28][CH3:29])(OCC)OCC>CO>[CH:7]1[CH:8]=[CH:9][CH:10]=[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:29]=[C:28]3[C:6]=12

Participants

4

Reactant 2

HCID 30713,3,-DiindolylmethaneHCID 31214Ethyl orthoformate

Product 1

HCID 114764Indolo(3,2-b)carbazoleYield 139.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In a 2000-ml three-necked flask that had been deaerated and filled with nitrogen were placed 50.69 g (0.2058 mole) of 3,3′-methylenediindole and 30.55 g (0.2061 mole) of triethyl orthoformate, then 640 g of methanol was added, and the mixture was stirred. To the mixture was added dropwise 5.0 g (0.0515 mole) of concentrated sulfuric over 3 minutes and the mixture was heated under reflux for 1 hour. The mixture was cooled to room temperature and the reddish brown crystals formed were collected by filtration and reslurried twice with 500 ml of methanol. The solvent was distilled off under reduced pressure and 36.81 g of solid C or indolo[3,2-b]carbazole (0.1438 mole, 69.9% yield) was obtained as a reddish brown powder.

Workup

  1. customIn a 2000-ml three-necked flask that had been deaerated
  2. additionfilled with nitrogen
  3. additionTo the mixture was added dropwise 5.0 g (0.0515 mole) of concentrated sulfuric over 3 minutes
  4. temperaturethe mixture was heated
  5. temperatureunder reflux for 1 hour
  6. customthe reddish brown crystals formed
  7. filtrationwere collected by filtration
  8. distillationThe solvent was distilled off under reduced pressure and 36.81 g of solid C

Sources & evidence

ORD record
ord-341a909424464318964f4b3b05ea5ee5
Source dataset
uspto-grants-2011_11
Patent number
US08062769B2

Reaction notes

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