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

HRID 361405

Reaction equation

HRID 361405 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 (2.0M) 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

  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-66ed24339d9542aeb83127d522d74002
Source dataset
uspto-grants-1999_02
Patent number
US05866579

Linked notes

Loading…