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

HRID 1597351Notes

Reaction equation

HRID 1597351 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 1N 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) eluting 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)
  5. washeluting with EtOAc/hexane (1:10)

Sources & evidence

ORD record
ord-90b3225b4b274c16a2bf665e8b5b0903
Source dataset
uspto-grants-2001_09
Patent number
US06294566B1

Reaction notes

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