Ammonia → 3-Nitro-7,8-dihydro-5H-pyrano[4,3-B]pyridine

HRID 1836290Notes

Reaction equation

HRID 1836290 reaction equation
C[N:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[C:4]([N+]([O-])=O)[C:3]1=O.[O:15]1[CH2:20]CC(=O)[CH2:17][CH2:16]1.N>CO>[N+:8]([C:6]1[CH:7]=[N:2][C:3]2[CH2:17][CH2:16][O:15][CH2:20][C:4]=2[CH:5]=1)([O-:10])=[O:9]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 121599Tetrahydro-4H-pyran-4-oneHCID 36212361-Methyl-3,5-dinitro-1H-pyridin-2-one

Product 1

HCID 107025123-Nitro-7,8-dihydro-5H-pyrano[4,3-B]pyridineYield 52.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 1-methyl-3,5-dinitro-2-pyridone (0.8 g, 4 mmol), tetrahydro-4H-pyran-4-one (0.4 g, 4 mmol) and ammonia solution in methanol (2.0 M, 40 mL) was refluxed for 4 h. 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 (0.376 g, 52% yield).

Workup

  1. temperaturewas refluxed for 4 h
  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-2f97ff08eb784c20a677865921299bb0
Source dataset
uspto-grants-2004_08
Patent number
US06777426B2

Reaction notes

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