Dimethylformamide → 3-Formyl-7-methyl-6-nitroindole
Reaction equation
P(Cl)(Cl)(Cl)=O.[CH3:6][C:7]1[C:8]([N+:16]([O-:18])=[O:17])=[CH:9][CH:10]=[C:11]2[C:15]=1[NH:14][CH:13]=[CH:12]2.[OH-].[Na+].CN(C)[CH:23]=[O:24]>>[CH:23]([C:12]1[C:11]2[C:15](=[C:7]([CH3:6])[C:8]([N+:16]([O-:18])=[O:17])=[CH:9][CH:10]=2)[NH:14][CH:13]=1)=[O:24]Participants
Conditions
- Temperature
- 35 °C
Procedure
Phosphorus oxychloride (0.878 mL, 9.42 mmol) is added to a stirred solution of dimethylformamide (5 mL). A solution of 7-methyl-6-nitroindole (1.5 g, 8.56 mmol) in dimethylformamide (2 mL) is added dropwise at room temperature at a rate so as to keep the temperature of the reaction mixture below 35° C. The solidified mixture is heated to 35° C. and stirred for 30 minutes. The reaction mixture is allowed to cool to room temperature and is treated with 25 mL of 5 N aqueous sodium hydroxide solution. This addition produces an exothermic reaction. This reaction mixture is extracted with ethyl acetate. The ethyl acetate is dried over magnesium sulfate, filtered and the solvents removed by rotary evaporation. The crude residue is recrystallized from ethyl alcohol to yield 1.3 g of 3-formyl-7-methyl-6-nitroindole as a yellow solid (74% yield).
Workup
- customthe temperature of the reaction mixture below 35° C
- temperatureto cool to room temperature
- additionThis addition
- customproduces
- customan exothermic reaction
- extractionThis reaction mixture is extracted with ethyl acetate
- dry with materialThe ethyl acetate is dried over magnesium sulfate
- filtrationfiltered
- customthe solvents removed by rotary evaporation
- customThe crude residue is recrystallized from ethyl alcohol
Sources & evidence
- ORD record
- ord-ee6592f8ceb54fcab3d83a66875d05a6
- Source dataset
- uspto-grants-2000_12
- Patent number
- US06162818
Reaction notes
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