Ammonia → 3-Nitro-8-methyl-5,6,7,8-tetrahydroquinoline

HRID 361399Notes

Reaction equation

HRID 361399 reaction equation
[CH3:1][CH:2]1[CH2:7][CH2:6][CH2:5][CH2:4][C:3]1=O.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[C:3]2[N:10]=[CH:15][C:14]([N+:16]([O-:18])=[O:17])=[CH:13][C:4]=2[CH2:5][CH2:6][CH2:7]1

Participants

4

Reactant 3

HCID 222AmmoniaHCID 114192-MethylcyclohexanoneHCID 36212361-Methyl-3,5-dinitro-1H-pyridin-2-one

Product 1

HCID 142970563-Nitro-8-methyl-5,6,7,8-tetrahydroquinolineYield 75%

Procedure

2-Methylcyclohexanone (170 mg, 1.52 mmol) was mixed with 1-methyl-3,5-dinitro-2-pyridone (296 mg, 1.49 mmol) in 1M methanolic ammonia (30 mL, 30 mmol) and heated at reflux for 3 h. The solvent was evaporated off and the residue was suspended in CHCl3 and flash chromatographed over silica gel (19 g) eluting with EtOAc/hexane (1:10) to afford a white solid (213 mg, 75% yield): mp 61°-63° C.

Workup

  1. temperatureheated
  2. temperatureat reflux for 3 h
  3. customThe solvent was evaporated off
  4. customflash chromatographed over silica gel (19 g)
  5. washeluting with EtOAc/hexane (1:10)

Sources & evidence

ORD record
ord-cccce10cb4624e419d24dbde486450f8
Source dataset
uspto-grants-1999_02
Patent number
US05866579

Reaction notes

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