Ammonia → 5,6-Dihydro-7,7-Dimethyl-3-nitro-cyclopenta[b]pyridine
Reaction equation
C[N:2]1[CH:7]=[C:6]([N+]([O-])=O)[CH:5]=[C:4]([N+:11]([O-:13])=[O:12])[C:3]1=O.[CH3:15][C:16]1(C)[CH2:20]C[CH2:18][C:17]1=O.N>CO>[CH3:15][C:16]1([CH3:20])[C:7]2=[N:2][CH:3]=[C:4]([N+:11]([O-:13])=[O:12])[CH:5]=[C:6]2[CH2:18][CH2:17]1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
A mixture of 1-methyl-3,5-dinitro-2-pyridone (0.8 g, 4.0 mmol), 2,2-dimethyl-cyclopentanone (0.45 g, 4.0 mmol) and ammonia solution (2.0M) in methanol (40 mL) was refluxed overnight. The solvent was removed in vacuo and the residue was dissolved in ethyl acetate. The soluble portion was flash chromatographed over silica gel (eluent 90:10 v/v ethyl acetate-hexane) to give a yellow solid (0.183 g, 24% yield).
Workup
- temperaturewas refluxed overnight
- customThe solvent was removed in vacuo
- dissolutionthe residue was dissolved in ethyl acetate
- customchromatographed over silica gel (eluent 90:10 v/v ethyl acetate-hexane)
Sources & evidence
- ORD record
- ord-66ed24339d9542aeb83127d522d74002
- Source dataset
- uspto-grants-1999_02
- Patent number
- US05866579
Reaction notes
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