Ammonia → 3-nitro-5,6,7,8-tetrahydroquinoline

HRID 1836287Notes

Reaction equation

HRID 1836287 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.[C:15]1(=O)[CH2:20]CC[CH2:17][CH2:16]1.N>CO>[N+:8]([C:6]1[CH:7]=[N:2][C:3]2[CH2:20][CH2:15][CH2:16][CH2:17][C:4]=2[CH:5]=1)([O-:10])=[O:9]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 7967CyclohexanoneHCID 36212361-Methyl-3,5-dinitro-1H-pyridin-2-one

Product 1

HCID 110303733-nitro-5,6,7,8-tetrahydroquinolineYield 94.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 1-methyl-3,5-dinitro-2-pyridone(2.4 g, 0.012 mole), cyclohexanone (1.18 g, 0.012 mole) and ammonia solution (2.0M, 120 mL) in methanol 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 (2.02 g, 94% 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-d32fcfb9d418435b93bdd87e5e3d2a1e
Source dataset
uspto-grants-2004_08
Patent number
US06777426B2

Reaction notes

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