Nitric Acid → 7-nitro-2,3,4,5-tetrahydro-1H-1-benzazepin-2-one
Reaction equation
[NH:1]1[C:7](=[O:8])[CH2:6][CH2:5][CH2:4][C:3]2[CH:9]=[CH:10][CH:11]=[CH:12][C:2]1=2.[N+:13]([O-])([OH:15])=[O:14].S(=O)(=O)(O)O>O>[N+:13]([C:10]1[CH:11]=[CH:12][C:2]2[NH:1][C:7](=[O:8])[CH2:6][CH2:5][CH2:4][C:3]=2[CH:9]=1)([O-:15])=[O:14]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
1,3,4,5-Tetrahydro-benzo[b]azepin-2-one (406 mg, 2.52 mmol) was added to a cooled (0° C.) mixture of nitric acid (5 ml) and sulfuric acid (7 ml). The mixture was stirred at 0° C. for 15 minutes, then poured into water (50 ml) and extracted with ethyl acetate (50 ml). The organic phase was washed once with aqueous sodium bicarbonate and once with water, and concentrated to a yellow solid. Trituration with ether afforded 7-Nitro-1,3,4,5-tetrahydro-benzo[b]azepin-2-one as an off-white solid, 276 mg. (53% yield) 1H NMR (400 MHz, DMSO-d6) δ 10.10 (s, 1H), 8.19 (s, 1H), 8.09-8.16 (m, 1H), 7.12-7.28 (m, 1H), 2.78-2.86 (m, 2H), 2.20-2.38 (m, 4H); MS (m/e) 207 (M+1).
Workup
- temperaturea cooled
- extractionextracted with ethyl acetate (50 ml)
- washThe organic phase was washed once with aqueous sodium bicarbonate and once with water
- concentrationconcentrated to a yellow solid
Sources & evidence
- ORD record
- ord-b95d3df9be124c2183a9b1d80cb0ff6c
- Source dataset
- uspto-grants-2013_10
- Patent number
- US08552186B2
Reaction notes
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