반응 #2151004

반응 방정식

sodium hydroxide

2-[(5-bromo-2,4,6,7-tetramethyl-2,3-dihydro-1-benzofuran-2-yl)methyl]-1H-isoindole-1,3(2H)-dione

Hydrazine monohydrate

hydrochloric acid

→

title compound

수율 69.0%

1-(5-bromo-2,4,6,7-tetramethyl-2,3-dihydro-1-benzofuran-2-yl)methanamine

수율 69.0%

용매

ethanol

반응 조건

후처리

1. 1
   기타synthesized in Reference Example 129
2. 2
   온도under heated
3. 3
   온도reflux for 3 hours
4. 4
   workup.STIRRINGby stirring
5. 5
   온도under heated
6. 6
   온도reflux for 1 hour
7. 7
   온도The reaction solution was cooled to room temperature
8. 8
   추출followed by extraction
9. 9
   세척The organic layer was washed with saturated saline
10. 10
    기타dried
11. 11
    농축followed by concentration under reduced pressure
12. 12
    기타The residue was purified by basic silica gel chromatography (hexane-ethyl acetate 80:20-0:100)

실험 절차

Hydrazine monohydrate (87 mg, 1.73 mmol) was added to a solution of ethanol (13 mL) containing 2-[(5-bromo-2,4,6,7-tetramethyl-2,3-dihydro-1-benzofuran-2-yl)methyl]-1H-isoindole-1,3(2H)-dione (530 mg, 1.28 mmol) synthesized in Reference Example 129, and the mixture was stirred under heated reflux for 3 hours. The reaction solution was cooled to room temperature, and 6N hydrochloric acid (10 mL) was added thereto, followed by stirring under heated reflux for 1 hour. The reaction solution was cooled to room temperature, and then 1N sodium hydroxide aqueous solution was added thereto to become weakly basic, followed by extraction using diisopropyl ether. The organic layer was washed with saturated saline, and dried using anhydrous magnesium sulfate, followed by concentration under reduced pressure. The residue was purified by basic silica gel chromatography (hexane-ethyl acetate 80:20-0:100) to give 250 mg of the title compound (yield: 69%).

출처