تفاعل #614751

معادلة التفاعل

5-nitro-2-(spiro[1-benzofuran-3,1′-cyclopropan]-4-yloxy)pyridine

Intermediate 86

5-nitro-2-(spiro[1-benzofuran-3,1′-cyclopropan]-4-yloxy)pyridine

water

ammonium chloride

→

title compound

المردود 96.0%

6-(spiro[1-benzofuran-3,1′-cyclopropan]-4-yloxy)-3-pyridinamine

المردود 96.0%

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 5-nitro-2-(spiro[1-benzofuran-3,1′-cyclopropan]-4-yloxy)pyridine (Intermediate 86, 99 mg) in tetrahydrofuran (5 ml)/water (2.5 ml) iron (97 mg, 1.741 mmol) and then ammonium chloride (93 mg, 1.741 mmol) were added and the reaction mixture was stirred for 4 hours 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 as a light yellow solid (85 mg).

المصدر