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

HRID 2289510Notes

Reaction equation

HRID 2289510 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) 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-be169c8df45443a1b30fd8584b529f19
Source dataset
uspto-grants-2000_07
Patent number
US06093727

Reaction notes

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