Sodium Hydroxide → 3-Chloro-1H-indol-4-amine
Reaction equation
[Cl:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[N+:11]([O-])=O)[NH:4][CH:3]=1.[OH-].[Na+]>C(O)C>[NH2:11][C:9]1[CH:8]=[CH:7][CH:6]=[C:5]2[C:10]=1[C:2]([Cl:1])=[CH:3][NH:4]2Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 45 °C
Procedure
Stannous chloride (4.59 g, 20.36 mmol) is added to a solution of 3-chloro-4-nitroindole in 50 mL of ethanol. The reaction is heated to 45° C. and stirred for 1.5 hours. The reaction is cooled to room temperature and treated with 1 M aqueous sodium hydroxide solution. This mixture is extracted with ethyl acetate. The combined organic extracts are dried over magnesium sulfate, filtered and the solvents removed by rotary evaporation. The crude residue is purified via silica gel column chromatography using 15% ethyl acetate/hexanes as the eluent. The appropriate fractions are combined and the solvents removed by rotary evaporation to yield 0.466 g of 4-amino-3-chloroindole as an off-white solid (55% yield).