Ammonia → HCID 23499159, compound

HRID 361400Notes

Reaction equation

HRID 361400 reaction equation
[CH2:1]([N:3]1[CH2:8][CH2:7][C:6](=O)[CH2:5][CH2:4]1)[CH3:2].C[N:11]1[CH:16]=[C:15]([N+:17]([O-:19])=[O:18])[CH:14]=C([N+]([O-])=O)C1=O.N>>[CH2:1]([N:3]1[CH2:8][CH2:7][C:6]2[N:11]=[CH:16][C:15]([N+:17]([O-:19])=[O:18])=[CH:14][C:5]=2[CH2:4]1)[CH3:2]

Participants

4

Reactant 3

HCID 222AmmoniaHCID 771591-Ethylpiperidin-4-oneHCID 36212361-Methyl-3,5-dinitro-1H-pyridin-2-one

Product 1

HCID 23499159HCID 23499159, compoundYield 93%

Procedure

1-Ethyl-4-piperidone (500 mg, 3.93 mmol) was mixed with 1-methyl-3,5-dinitro-2-pyridone (392 mg, 1.97 miol) in 1M methanolic ammonia (40 mL, 40 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 (32 g) eluting with EtOAc to afford an orange solid (379 mg, 93% yield).

Workup

  1. temperatureheated
  2. temperatureat reflux for 3 h
  3. customThe solvent was evaporated off
  4. customflash chromatographed over silica gel (32 g)
  5. washeluting with EtOAc

Sources & evidence

ORD record
ord-ea85bf1c43c043deaad087c68fd3ec45
Source dataset
uspto-grants-1999_02
Patent number
US05866579

Reaction notes

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