反応 #946795

反応方程式

4′-fluoro-biphenyl-3,4-diamine

4-hydroxycoumarin

→

7-(4-fluoro-phenyl)-4-(2-hydroxy-phenyl)-1,3-dihydro-benzo[b][1,4]diazepin-2-one

収率 112.6%

title compound

8-(4-Fluoro-phenyl)-4-(2-hydroxy-phenyl)-1,3-dihydro-benzo[b][1,4]diazepin-2-one

溶媒

xylene

ethyl acetate

hexane

反応条件

後処理

1. 1
   その他to form after ca. 1 h
2. 2
   温度The mixture was cooled to 23° C.
3. 3
   ろ過The precipitate was collected by filtration
4. 4
   その他triturated with ethyl acetate/hexane (1:1)

実験手順

A mixture of 4′-fluoro-biphenyl-3,4-diamine (prepared from (3-amino-4′-fluoro-biphenyl-4-yl)-carbamic acid tert.-butyl ester (Example G39) by treatment with TFA) (121 mg, 0.6 mmol) and 4-hydroxycoumarin (97 mmol, 0.6 mmol) in xylene (8 mL) was heated to 130° C. for 6 h. A yellow precipitate started to form after ca. 1 h. The mixture was cooled to 23° C., diluted with ethyl acetate (8 mL) and hexane (8 mL) and stirring was continued for 15 min. The precipitate was collected by filtration and triturated with ethyl acetate/hexane (1:1) to give the title compound as a mixture with the isomeric 7-(4-fluoro-phenyl)-4-(2-hydroxy-phenyl)-1,3-dihydro-benzo[b][1,4]diazepin-2-one as yellow solid (117 mg).

出典