反应详情

温度

160 °C

To a solution of 6-iodoindan-5-amine (135 mg, 0.52 mmol) in DMF (2 mL), was added copper (I) cyanide (93 mg, 1.04 mmol). The mixture was heated at 160° C. for 1.5 h. The reaction mixture was poured into 10% NH4OH. An equal amount of dichloromethane was added and resulting mixture was filtered. The filtrate was partitioned between two layers. The aqueous layer was extracted with dichloromethane (1×). The combined organic layers were concentrated in vacuo. The residue was dissolved in ethyl ether. The ether layer was washed with aqueous sodium bisulfite, dried with Na2SO4 and concentrated in vacuo. The residue was purified by flash chromatography (Si, hexanes/EtOAc) yielding 6-aminoindane-5-carbonitrile (48.5 mg, 59%). LCMS calc.=158.08; found=159.1 (M+1)+. 1H NMR (500 MHz, CDCl3) δ 7.22 (s, 1H), 6.64 (s, 1H), 4.25 (br, s, 2H), 2.85 (t, J=7.4 Hz, 2H), 2.80 (t, J=7.4 Hz, 2H), 2.09-2.03 (m, 2H).

1. customresulting mixture
2. filtrationwas filtered
3. customThe filtrate was partitioned between two layers
4. extractionThe aqueous layer was extracted with dichloromethane (1×)
5. concentrationThe combined organic layers were concentrated in vacuo
6. dissolutionThe residue was dissolved in ethyl ether
7. washThe ether layer was washed with aqueous sodium bisulfite
8. dry with materialdried with Na2SO4
9. concentrationconcentrated in vacuo
10. customThe residue was purified by flash chromatography (Si, hexanes/EtOAc)