تفاعل #1571817

معادلة التفاعل

2-(7-methylspiro[2H-benzofuran-3,1′-cyclopropane]-4-yl)oxy-5-nitro-pyridine

Intermediate 14

2-(7-methylspiro[2H-benzofuran-3,1′-cyclopropane]-4-yl)oxy-5-nitro-pyridine

water

ammonium chloride

→

title compound

المردود 85.2%

6-(7-methylspiro[2H-benzofuran-3,1′-cyclopropane]-4-yl)oxypyridin-3-amine

المردود 85.2%

المذيبات

tetrahydrofuran

ظروف التفاعل

المعالجة

1. 1
   ترشيحThe catalyst was filtered off
2. 2
   workup.ADDITIONthe residue was diluted with an aqueous saturated solution of NaHCO3 (5 ml)
3. 3
   استخلاصextracted with ethyl acetate (3×10 ml)
4. 4
   تجفيفThe organic layer was dried over sodium sulphate
5. 5
   ترشيحfiltered
6. 6
   أخرىevaporated
7. 7
   أخرىthe residue was purified by flash chromatography (Biotage system) on silica gel using a 10 g SNAP column and cyclohexane/ethyl acetate 8:2 to cyclohexane/ethyl acetate 1:1 as eluents

الإجراء التجريبي

To a solution of 2-(7-methylspiro[2H-benzofuran-3,1′-cyclopropane]-4-yl)oxy-5-nitro-pyridine (Intermediate 14, 265 mg) in tetrahydrofuran (5 ml)/water (2.5 ml) iron (245 mg, 4.45 mmol) and then ammonium chloride (238 mg, 4.45 mmol) were added and the reaction mixture was stirred overnight at room temperature. The catalyst was filtered off and the residue was diluted with an aqueous saturated solution of NaHCO3 (5 ml) and extracted with ethyl acetate (3×10 ml). The organic layer was dried over sodium sulphate, filtered and evaporated and the residue was purified by flash chromatography (Biotage system) on silica gel using a 10 g SNAP column and cyclohexane/ethyl acetate 8:2 to cyclohexane/ethyl acetate 1:1 as eluents affording the title compound (203 mg) as a light yellow solid.

المصدر