Ammonia → 5,6,7,8-Tetrahydro-7-methyl-3-nitro-quinoline

HRID 1836284Notes

Reaction equation

HRID 1836284 reaction equation
[CH3:1][CH:2]1[CH2:7][CH2:6][CH2:5][C:4](=O)[CH2:3]1.C[N:10]1[CH:15]=[C:14]([N+:16]([O-:18])=[O:17])[CH:13]=C([N+]([O-])=O)C1=O.N>>[CH3:1][CH:2]1[CH2:3][C:4]2[N:10]=[CH:15][C:14]([N+:16]([O-:18])=[O:17])=[CH:13][C:5]=2[CH2:6][CH2:7]1

Participants

4

Reactant 3

HCID 222AmmoniaHCID 115673-MethylcyclohexanoneHCID 36212361-Methyl-3,5-dinitro-1H-pyridin-2-one

Product 1

HCID 234992195,6,7,8-Tetrahydro-7-methyl-3-nitro-quinolineYield 63%

Procedure

3-Methylcyclohexanone (0.56 g, 4.99 mmol) was mixed with 1-methyl-3,5-dinitro-2-pyridone(1.00 g, 5.02 mmol) in 1M methanolic ammonia (50 mL, 50 mmol) and heated at reflux overnight. The solvent was evaporated off and the residue was suspended in CHCl3 and flash chromatographed over silica gel (43 g) eluding with EtOAc/hexane (1:10) to afford a white solid (515 mg, 63% yield): mp 55-56° C.

Workup

  1. temperatureheated
  2. temperatureat reflux overnight
  3. customThe solvent was evaporated off
  4. customflash chromatographed over silica gel (43 g)

Sources & evidence

ORD record
ord-e53bbb933754486fb547a97e60dc03d7
Source dataset
uspto-grants-2004_08
Patent number
US06777426B2

Reaction notes

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