Methanol → HCID 70224214, compound
Reaction equation
[Na].[CH3:2][C:3]1[N+:8]([O-:9])=[C:7]2[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:6]2=[C:5]([N+]([O-])=O)[C:4]=1[C:18]([O:20][CH2:21]C)=[O:19].[CH3:23][OH:24]>>[CH3:23][O:24][C:5]1[C:4]([C:18]([O:20][CH3:21])=[O:19])=[C:3]([CH3:2])[N+:8]([O-:9])=[C:7]2[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:6]=12Participants
Procedure
In an atmosphere of argon and at room temperature, metallic sodium (86.0 mg, 0.005 g atom) was dissolved in anhydrous methanol (8.0 ml) to which was subsequently added dropwise methanol solution (20.0 ml) of ethyl 2-methyl-4-nitro-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridine-3-carboxylate N-oxide (1.00 g, 3.40 mmol), and the resulting mixture was stirred at room temperature for 29 hours. After evaporation of the solvent under reduced pressure, the resulting residue was mixed with water and extracted with chloroform, and the thus obtained organic layer was washed with water and saturated brine in that order and dried over anhydrous sodium sulfate. After evaporation of the solvent under reduced pressure, the resulting residue was purified by a silica gel column chromatography (ethyl acetate:hexane=5:1—ethyl acetate:methanol=15:1) to obtain the title compound (777.9 mg, 86.3%) as pale yellow powder.
Workup
- customAfter evaporation of the solvent under reduced pressure
- additionthe resulting residue was mixed with water
- extractionextracted with chloroform
- washthe thus obtained organic layer was washed with water and saturated brine in that order
- dry with materialdried over anhydrous sodium sulfate
- customAfter evaporation of the solvent under reduced pressure
- customthe resulting residue was purified by a silica gel column chromatography (ethyl acetate:hexane=5:1—ethyl acetate:methanol=15:1)
Sources & evidence
- ORD record
- ord-a7942c820fb646f18a85f27d965caa0b
- Source dataset
- uspto-grants-2001_07
- Patent number
- US06258829B1
Reaction notes
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