Ammonia → 6-Ethyl-5,6,7,8-tetrahydro-3-nitro-1,6-naphthyridine

HRID 1597353Notes

Reaction equation

HRID 1597353 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 234991596-Ethyl-5,6,7,8-tetrahydro-3-nitro-1,6-naphthyridineYield 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 mmol) 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-75f7bba5527d47a1adca56fad14a4991
Source dataset
uspto-grants-2001_09
Patent number
US06294566B1

Reaction notes

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