Carbon Dioxide → 3,3'-Diindolylmethane

HRID 2061003Notes

Reaction equation

HRID 2061003 reaction equation
[CH:1]1[CH:2]=[CH:3][C:4]2[NH:9][CH:8]=[C:7]([CH2:10]O)[C:5]=2[CH:6]=1.C(=O)=O>[OH-].[Na+]>[CH:1]1[CH:2]=[CH:3][C:4]2[NH:9][CH:8]=[C:7]([CH2:10][C:7]3[C:5]4[CH:6]=[CH:1][CH:2]=[CH:3][C:4]=4[NH:9][CH:8]=3)[C:5]=2[CH:6]=1

Participants

4

Reactant 2

HCID 280Carbon DioxideHCID 3712Indole-3-carbinol

Product 1

HCID 30713,3'-DiindolylmethaneYield 77.7%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

Part (a). Indole-3-carbinol (1.0 g, 6.79 mmol) in 10% aqueous NaOH solution (100 mL) was refluxed for 1 h. The solution was cooled, neutralized with carbon dioxide and the white precipitate was collected by filtration, which was then crystallized from toluene to yield 3,3′-Diindolylmethane as a white solid (0.65 g, 77%): 1H NMR (300 MHz, CDCl3) δ 4.26 (s, 2, CH2), 6.94 (m, 2, PyH), 7.11 (m, 2, ArH), 7.21 (m, 2, ArH), 7.36 (m, 2, ArH), 7.64 (m, 2, ArH), 7.86 (br. s, 2, NH).

Workup

  1. temperatureThe solution was cooled
  2. filtrationthe white precipitate was collected by filtration, which
  3. customwas then crystallized from toluene

Sources & evidence

ORD record
ord-4cc08e4143de41ae8efd19d10ebd2ad9
Source dataset
uspto-grants-2012_10
Patent number
US08278341B2

Reaction notes

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