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 CH2Cl2 was added and resulting mixture was filtered. The filtrate was partitioned between two layers. The aqueous layer was extracted with CH2Cl2 (1×). The combined organic layers were concentrated in vacuo. The residue was dissolved in Et2O. The Et2O layer was washed with aqueous Na2S2O3, dried (Na2SO4) and concentrated in vacuo. The residue was purified by flash chromatography (Si, hexanes/EtOAc) yielding 6-aminoindane-5-carbonitrile. LCMS calc.=159.1; 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 CH2Cl2 (1×)
5. concentrationThe combined organic layers were concentrated in vacuo
6. dissolutionThe residue was dissolved in Et2O
7. washThe Et2O layer was washed with aqueous Na2S2O3
8. dry with materialdried (Na2SO4)
9. concentrationconcentrated in vacuo
10. customThe residue was purified by flash chromatography (Si, hexanes/EtOAc)