N,N-Dimethylaniline → 2-Phenylindole
Reaction equation
CO[C:3]1[CH:8]=[CH:7][C:6]([NH2:9])=[CH:5][CH:4]=1.CN(C)C1C=CC=CC=1.CO[C:21]1[CH:26]=[CH:25][C:24]([C:27]([CH2:29]Br)=O)=[CH:23][CH:22]=1>CCOC(C)=O>[C:24]1([C:27]2[NH:9][C:6]3[C:7]([CH:29]=2)=[CH:8][CH:3]=[CH:4][CH:5]=3)[CH:25]=[CH:26][CH:21]=[CH:22][CH:23]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a boiling mixture of in-anisidine (1.56 ml, 20.0 minol) and N,N-dimethylaniline (3.5 ml) was added 2-bromo-4-methoxyacetophenone (1.37 g in EtOAc, 6.00 mmol) slowly by syringe. After addition, the mixture was kept at 170° C. for 1 hour. The reaction mixture was cooled to room temperature and a dark colored solid was formed. EtOAc was added along with HCI (2 N). The aqueous layer was extracted with EtOAc several times. The combined organic layers were washed with brine, and dried over MgSO4. Solvent was removed under the reduced pressure to afford a dark brown colored solid. Purification by recrystallization in EtOH afforded indole 31 as a white crystallinc material.