Ethylenediamine → 9-Nitro-1,2,3,4-tetrahydro-5H-1,4-benzodiazepin-5-one

HRID 1040950Notes

Reaction equation

CO[C:3](=[O:14])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([N+:10]([O-:12])=[O:11])[C:5]=1Cl.C([O-])([O-])=O.[Na+].[Na+].[CH2:21]([NH2:24])[CH2:22][NH2:23]>C(O)CCC>[N+:10]([C:6]1[C:5]2[NH:23][CH2:22][CH2:21][NH:24][C:3](=[O:14])[C:4]=2[CH:9]=[CH:8][CH:7]=1)([O-:12])=[O:11]

Participants

Conditions

Temperature: 80 °C

Procedure

2-Chloro-3-nitro-benzoic acid methyl ester (2.00 g, 9.3 mmol) was dissolved in n-butanol (10 ml). Na2CO3 (986 mg, 9.3 mmol) was added followed by ethylenediamine (622 μL, 9.3 mmol). The reaction mixture was heated to 80° C. for 16 h. The reaction mixture was cooled, filtered, and washed with water (200 ml) to afford 9-Nitro-1,2,3,4-tetrahydro-benzo[e][1,4]diazepin-5-one as a bright orange solid (900 mg, 46%). mp 196-197° C.; LCMS: m/z=208.22 (M+H+); 1H NMR (400 MHz, DMSO-d6) δ 8.70 (m, 1H), 8.39 (m, 1H), 8.22 (dd, J=8.3 Hz, 1.8 Hz, 1H), 8.14 (dd, J=7.8 Hz, 1.8 Hz, 1H), 6.75 (t, J=7.8 Hz, 1H), 3.65 (m, 2H), 3.35 (m, 2H).

Workup

temperatureThe reaction mixture was cooled
filtrationfiltered
washwashed with water (200 ml)

Sources & evidence

ORD record: ord-77906f590c064b8b9811e287318bd70e
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08552186B2

Reaction notes

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