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17450-69-0

benzofuran-6-ylMethanaMine synthesis

4synthesis methods
17450-68-9 Synthesis
BENZOFURAN-6-CARBONITRILE

17450-68-9
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Yield:17450-69-0 48.6%

Reaction Conditions:

with lithium aluminium hydride in tetrahydrofuran at 20; for 1 h;

Steps:

Benzofuran-6-ylmethanamine (14)

To a mixture of LiAlH4 (265 mg, 6.99 mmol) in THF(10.0 mL), compound 13 (1.00 g, 6.99 mmol) was added inone portion at 20 °C. The mixture was stirred at 20 °C for1 h. TLC indicated one new spot was detected. 1 mL ofsaturated Na2SO4 was added to the reaction mixture carefully,and then filtered. The filtration was concentrated togive compound 14 (0.5 g, 3.40 mmol, 48.60% yield) as alight yellow oil. 1H NMR (MeOD, 400 MHz) δ 7.71(d, J = 2.0 Hz, 1H, H-2), 7.55 (d, J = 8.0 Hz, 1H, H-4), 7.49(s, 1H, H-7), 7.21 (d, J = 8.0 Hz, 1H, H-5), 6.79-6.80 (m,1H, H-3), 3.88 (s, 2H, CH2, CH2NH2); LCMS m/z 148.1[M + H]+.

References:

Du, Guoxin;Du, Weiwei;An, Yuanlong;Wang, Minnan;Hao, Feifei;Tong, Xiaochu;Gong, Qi;He, Xiangdong;Jiang, Hualiang;He, Wei;Zheng, Mingyue;Zhang, Donglei [Medicinal Chemistry Research,2022,vol. 31,# 4,p. 555 - 579]