Ammonia → 5,6-Dihydro-7,7-Dimethyl-3-nitro-cyclopenta[b]pyridine

HRID 1597359Notes

Reaction equation

HRID 1597359 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]1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 1382862,2-DimethylcyclopentanoneHCID 36212361-Methyl-3,5-dinitro-1H-pyridin-2-one

Product 1

HCID 234991895,6-Dihydro-7,7-Dimethyl-3-nitro-cyclopenta[b]pyridineYield 24%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

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 (2.0 M) 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

  1. temperaturewas refluxed overnight
  2. customThe solvent was removed in vacuo
  3. dissolutionthe residue was dissolved in ethyl acetate
  4. customchromatographed over silica gel (eluent: 90:10 v/v ethyl acetate-hexane)

Sources & evidence

ORD record
ord-c4ce44e06dd941e29cd8a8def0734e5b
Source dataset
uspto-grants-2001_09
Patent number
US06294566B1

Reaction notes

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