4-chloro-3-propan-2-ylaniline

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2.8 g of anhydrous potassium carbonate and 2.0 g of -chloro-2-butene were added to 3.2 g of 4-chloro-3-isopropylaniline in 15 ml of N,N-dimethylformamide, followed by stirring at 70°-90° C. for 1 hour. After potassium carbonate was removed by filtration, 100 ml of water were added, and extraction was then carried out with toluene. After drying over anhydrous sodium sulfate, the reaction solution was concentrated by means of an evaporator, and silica gel chromatography was then done to obtain 1.5 g of the desired compound. After potassium carbonate was removed by filtration, 100 ml of water were added extraction After drying over anhydrous sodium sulfate the reaction solution was concentrated by means of an evaporator, and silica gel chromatography

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2.8 g of anhydrous potassium carbonate and 2.0 g of -chloro-2-butene were added to 3.2 g of 4-chloro-3-isopropylaniline in 15 ml of N,N-dimethylformamide, followed by stirring at 70°-90° C. for 1 hour. After potassium carbonate was removed by filtration, 100 ml of water were added, and extraction was then carried out with toluene. After drying over anhydrous sodium sulfate, the reaction solution was concentrated by means of an evaporator, and silica gel chromatography was then done to obtain 1.5 g of the desired compound. After potassium carbonate was removed by filtration, 100 ml of water were added extraction After drying over anhydrous sodium sulfate the reaction solution was concentrated by means of an evaporator, and silica gel chromatography

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Amounts used: 25 mL of acetic acid was saturated with sulfur dioxide, 671 mg of copper(I) chloride, 4.60 g (27.1 mmol) of 4-chloro-3-isopropyl-phenylamine dissolved in a mixture of 4 mL of acetic acid and 9 mL of concentrated hydrochloric acid, 2.3 g of sodium nitrite in 10 mL of water. Flash chromatography on silica using 3-20% ethyl acetate in hexanes afforded 2.18 g of the product as a white solid. LC-MSD spectrum not observed.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Prepared from 7.84 g of 3-iso-propyl-phenylamine and 7.75 g NCS. Yield: 4.6 g. LC-MSD, m/z for C9H12ClN [M+H]+=170.2, 172.0;

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2.8 g of anhydrous potassium carbonate and 2.0 g of -chloro-2-butene were added to 3.2 g of 4-chloro-3-isopropylaniline in 15 ml of N,N-dimethylformamide, followed by stirring at 70°-90° C. for 1 hour. After potassium carbonate was removed by filtration, 100 ml of water were added, and extraction was then carried out with toluene. After drying over anhydrous sodium sulfate, the reaction solution was concentrated by means of an evaporator, and silica gel chromatography was then done to obtain 1.5 g of the desired compound. After potassium carbonate was removed by filtration, 100 ml of water were added extraction After drying over anhydrous sodium sulfate the reaction solution was concentrated by means of an evaporator, and silica gel chromatography