Methanol → 6-Nitro-2,3,4,5-tetrahydro-1H-benzo[e][1,4]diazepine

6-Nitro-1,2,3,4-tetrahydro-benzo[e][1,4]diazepin-5-one (1.20 g, 5.8 mmol) was dissolved in THF (50 mL) and the solution was treated with 1N Borane-THF (2.77 mL, 28.95 mmol). The reaction mixture was then refluxed overnight. Upon cooling, the solution was treated with methanol (50 mL) and was then reduced in vacuo. The residue was taken up in ethyl acetate (40 mL) and was washed with saturated NaHCO3 (100 mL). Organics were extracted with ethyl acetate (3×40 mL) and were then dried over Na2SO4, filtered and reduced. The product was then purified and isolated by flash column chromatography (0% MeOH/DCM-30% MeOH/DCM) to afford 140 mg of 6-Nitro-2,3,4,5-tetrahydro-1H-benzo[e][1,4]diazepine as a yellow oil. LC/MS (ESI)=194.32 (M+H). 1H NMR (400 MHz, CDCl3) δ 7.26 (m, 2H), 7.06 (d, 1H, J=8.08 Hz), 6.86 (d, 1H), J=8.34 Hz), 5.32 (s, 1H), 4.66 (s, 2H), 3.24 (t, 2H, J=5.05 Hz), 3.00 (t, 2H, J=5.05 Hz).

1. temperatureThe reaction mixture was then refluxed overnight
2. temperatureUpon cooling
3. washwas washed with saturated NaHCO3 (100 mL)
4. extractionOrganics were extracted with ethyl acetate (3×40 mL)
5. dry with materialwere then dried over Na2SO4
6. filtrationfiltered
7. customThe product was then purified
8. customisolated by flash column chromatography (0% MeOH/DCM-30% MeOH/DCM)

ORD record

ord-52deeaab39b7404f8984e7033685c34c

Source dataset

uspto-grants-2013_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08552186B2