Nitric Acid → HCID 86707693, compound
Reaction equation
[OH:1][C:2]1[C:6]2([CH2:11][CH2:10][N:9]([O:12][CH3:13])[CH2:8][CH2:7]2)[N:5]([CH3:14])[C:4](=[O:15])[C:3]=1[C:16]1[C:21]([CH3:22])=[CH:20][C:19]([CH3:23])=[CH:18][C:17]=1[CH3:24].[N+:25]([O-])([OH:27])=[O:26]>C(Cl)(Cl)Cl>[CH3:13][O:12][N:9]1[CH2:10][CH2:11][C:6]2([N:5]([CH3:14])[C:4](=[O:15])[C:3]([N+:25]([O-:27])=[O:26])([C:16]3[C:21]([CH3:22])=[CH:20][C:19]([CH3:23])=[CH:18][C:17]=3[CH3:24])[C:2]2=[O:1])[CH2:7][CH2:8]1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a solution of 4-hydroxy-8-methoxy-1-methyl-3-(2,4,6-trimethyl-phenyl)-1,8-diaza-spiro[4.5]dec-3-en-2-one (compound P2.2) (150 mg, 0.454 mmol) in chloroform (5 ml) at −5° C. was added fuming nitric acid (0.038 ml, 57.8 mg, 0.917 mmol) in chloroform (0.5 ml) dropwise. The reaction mixture was stirred at 0° C. for 30 minutes and at room temperature for three days, poured on ice water (10 ml), the layers were separated, the water phase extracted with ethyl acetate (3×20 ml), the combined organic phases washed with water (15 ml) and brine (15 ml), dried over sodium sulfate and concentrated. The residue was purified by chromatography on silica gel (ethyl acetate/cyclohexane 1:3). Yield: 90 mg of 8-methoxy-1-methyl-3-nitro-3-(2,4,6-trimethyl-phenyl)-1,8-diaza-spiro[4.5]decane-2,4-dione (title compound P1.13) as a white solid, mp 127-129° C.
Workup
- additionpoured on ice water (10 ml)
- customthe layers were separated
- extractionthe water phase extracted with ethyl acetate (3×20 ml)
- washthe combined organic phases washed with water (15 ml) and brine (15 ml)
- dry with materialdried over sodium sulfate
- concentrationconcentrated
- customThe residue was purified by chromatography on silica gel (ethyl acetate/cyclohexane 1:3)
Sources & evidence
- ORD record
- ord-830d713411304bff8665c035e842180b
- Source dataset
- uspto-grants-2015_05
- Patent number
- US09023760B2
Reaction notes
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