Dimethylformamide → Indole

HRID 50525Notes

Reaction equation

HRID 50525 reaction equation
[CH3:1][N:2]([CH:4]=O)C.N[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1S.CC(OC(C)=O)=O>C1C=CC=CC=1>[NH:2]1[C:1]2[C:12](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:11]=[CH:4]1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 7918Acetic AnhydrideHCID 87132-Aminothiophenol

Product 1

HCID 798IndoleYield 32%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
60 °C

Procedure

A dry DMF solution of the compound (A-2) (0.01 mole) was added o-aminothiophenol (0.013 mole) and Ac2O (0.5ml) at room temperature. The mixture was stirred at 60° C. for 3 h. The reaction mixture was poured into stirred benzene and the precipitated solid was collected by filtration. The crude solid was washed with MeOH and recrystallized from benzene to afford target compound (A) (32% yield). 1H-NMR spectrum is shown in FIG. 3. Photoluminescence spectrum is shown in FIG. 4.

Workup

  1. additionThe reaction mixture was poured
  2. filtrationthe precipitated solid was collected by filtration
  3. washThe crude solid was washed with MeOH
  4. customrecrystallized from benzene

Sources & evidence

ORD record
ord-ea6e5be525964d0ca63bb25dbda0176d
Source dataset
uspto-grants-2004_03
Patent number
US06713194B2

Reaction notes

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