反応 #161408

反応方程式

hydrogen

potassium carbonate

cyclopropylamine

2-(4-fluoro-3-nitrophenyl)benzoxazole

→

title compound

収率 46.0%

2-(2-cyclopropylaminoanilin-5-yl)benzoxazole

収率 46.0%

溶媒

water

ethanol

反応条件

後処理

1. 1
   温度this was heated
2. 2
   温度to reflux for 7 hours
3. 3
   ろ過the precipitated crystals were filtered
4. 4
   洗浄washed with water
5. 5
   その他dried
6. 6
   その他To a tetrahydrofuran solution (5 mL) of the crystals obtained
7. 7
   ろ過this was filtered through Celite
8. 8
   濃縮the filtrate was concentrated
9. 9
   その他The residue obtained
10. 10
    その他was purified by silica gel column chromatography

実験手順

To a suspension of 2-(4-fluoro-3-nitrophenyl)benzoxazole (see Working Example 15-2) (300 mg, 1.16 mmol) in ethanol (5 mL) was added potassium carbonate (176 mg, 1.28 mmol) and cyclopropylamine (99.3 mg, 1.74 mmol), and this was heated to reflux for 7 hours. After the reaction was complete, this was cooled to room temperature, water was added, and the precipitated crystals were filtered, washed with water and then dried. To a tetrahydrofuran solution (5 mL) of the crystals obtained was added 10% palladium-carbon (50 mg). A hydrogen atmosphere was substituted in the flask, and this was stirred at room temperature for 14 hours. After the reaction was complete, this was filtered through Celite and the filtrate was concentrated. The residue obtained was purified by silica gel column chromatography to yield the title compound (141 mg, 46% yield).

出典