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8-FLUORO-2,3,4,5-TETRAHYDRO-1H-BENZO[E][1,4]DIAZEPINE synthesis

4synthesis methods
-

Yield:620948-83-6 77.2%

Reaction Conditions:

with lithium aluminium tetrahydride in tetrahydrofuran at 0 - 60; for 12 h;

Steps:

4.9.1 8-Fluoro-2,3,4,5-tetrahydro-1H-benzo[e][1,4]diazepine (2c)

To a solution of 8-fluoro-3,4-dihydro-1H-benzo[e][1,4]diazepine-2,5-dione (1.6g, 8.24mmol) in THF (30mL) was added 2M solution of LAH in THF (20.6mL, 41.2mmol) at 0°C and stirred for 12h at 60°C. The progress of the reaction was monitored by TLC. The crude residue was quenched with ice and extracted with dichloromethane. The combined organic layers were dried over anhydrous sodium sulfate, concentrated to get crude residue. The crude residue was purified by gradient column chromatography using methanol in dichloromethane to give the title compound as a yellow liquid (1.05g, 77.2%). 1H NMR (400MHz, DMSO-d6): δ 7.01 (t, J=7.2Hz, 1H), 6.51 - 6.44 (m, 2H), 3.84 (s, 2H), 3.11 - 3.09 (m, 2H), 3.04 - 3.02 (m, 2H).

References:

Tamizharasan, Natarajan;Gajendran, Chandru;Kristam, Rajendra;Sulochana, Suresh P.;Sivanandhan, Dhanalakshmi;Mullangi, Ramesh;Mathivathanan, Logesh;Hallur, Gurulingappa;Suresh, Palaniswamy [Bioorganic Chemistry,2020,vol. 99,art. no. 103800]

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