Sodium Hydroxide → 3'-Amino-4'-fluoroacetophenone

To a stirred mixture of 3'-nitro-4'-fluoroacetophenone (10.04 g, 55 mmol) in 72 mL of concentrated hydrochloric acid, was added tin (II) chloride dihydrate (37 grams), in portions. After approximately one third of the material had been added, a rapid rise in the internal reaction temperature (to 95° C.) was noted. The mixture was then heated to reflux for 10 minutes, this resulted in the dissolution of all solids to give a solution. The mixture was then cooled to room temperature and poured onto an ice/water mixture (150 g). The mixture was then further cooled in an ice bath while 50% sodium hydroxide was added until pH 12 was reached. The aqueous layer was extracted twice with ether (50 mL). The combined organic extracts were washed with brine and then dried over sodium sulfate. Removal of the drying agent and in vacuo concentration of the filtrate afforded a yellow-orange oil (8.73 g) which was recrystallized on standing. This material was of sufficient purity to be used directly in the next step (Part 3).

1. additionAfter approximately one third of the material had been added
2. customin the internal reaction temperature (to 95° C.)
3. temperatureThe mixture was then heated
4. temperatureto reflux for 10 minutes
5. customthis resulted in the dissolution of all solids
6. customto give a solution
7. additionwas added until pH 12
8. extractionThe aqueous layer was extracted twice with ether (50 mL)
9. washThe combined organic extracts were washed with brine
10. dry with materialdried over sodium sulfate
11. customRemoval of the drying agent

ORD record

ord-f425ff543a5844d183f937cfee35d29d

Source dataset

uspto-grants-2000_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06153604