5-fluoro-3-methyl-1,3-dihydroindol-2-one

Conditions: temp:70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Under an argon atmosphere 18 mL (18 mmol) of a 1M borane in THF solution was added dropwise to 1.5 g (9.1 mmol) 5-fluoro-3-methyl-1,3-dihydro-indol-2-one in 50 mL THF. The reaction mixture was stirred for 2 h at 70° C., cooled to 0° C. and combined with 10 mL methanol and then with 30 mL semi-concentrated hydrochloric acid solution. The reaction mixture was refluxed for 1 h with stirring, cooled and the organic phase was eliminated using the rotary evaporator. The aqueous phase was extracted with ethyl acetate. The aqueous phase was made alkaline with an aqueous 4M sodium hydroxide solution and extracted with dichloromethane. The organic phase was dried on sodium sulphate, filtered off and evaporated down. cooled to 0° C. The reaction mixture was refluxed for 1 h with stirring cooled the rotary evaporator The aqueous phase was extracted with ethyl acetate extracted with dichloromethane The organic phase was dried on sodium sulphate filtered off evaporated down

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

Procedure: 3.0 g (20 mmol) 5-fluoro-1,3-dihydro-indol-2-one, 50 mL methanol and 2.0 g Raney nickel were stirred for 1.5 h at 200° C. in an autoclave. After the catalyst had been filtered off the mother liquor was evaporated down and the residue was recrystallised from methanol. After the catalyst had been filtered off the mother liquor was evaporated down the residue was recrystallised from methanol

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

Procedure: 3.0 g (20 mmol) 5-fluoro-1,3-dihydro-indol-2-one were stirred with 2.0 g Raney nickel in 50 mL methanol for 1.5 h at 200° C. in an autoclave. The catalyst was filtered off and the filtrate was concentrated to dryness by rotary evaporation. The residue was recrystallised from methanol, suction filtered and dried. The catalyst was filtered off the filtrate was concentrated to dryness by rotary evaporation The residue was recrystallised from methanol, suction filtered dried