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

HRID 1836286Notes

Reaction equation

HRID 1836286 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-b4c5261fb9944d948516e9f4c869d30b
Source dataset
uspto-grants-2004_08
Patent number
US06777426B2

Reaction notes

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