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

HRID 2289511Notes

Reaction equation

HRID 2289511 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-a24322b0f71142ca818d815b52acec3d
Source dataset
uspto-grants-2000_07
Patent number
US06093727

Reaction notes

Loading…