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

HRID 1066767Notes

Reaction equation

HRID 1066767 reaction equation
[N+]([C:4]1[C:5](=O)[N:6](C)[CH:7]=[C:8]([N+:10]([O-:12])=[O:11])[CH:9]=1)([O-])=O.N.[CH3:16][N:17]1[CH2:22]CC(=O)[CH2:19][CH2:18]1>CO>[CH3:16][N:17]1[CH2:18][CH2:19][C:5]2[N:6]=[CH:7][C:8]([N+:10]([O-:12])=[O:11])=[CH:9][C:4]=2[CH2:22]1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 740491-Methyl-4-piperidoneHCID 36212361-Methyl-3,5-dinitro-1H-pyridin-2-one

Product 1

HCID 142970606-Methyl-3-nitro-5,6,7,8-tetrahydro-1,6-naphthyridineYield 59%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3,5-Dinitro-1-methyl-2-pyridone (5.97 g; 30 mmol) was treated with 1.22M ammonia in methanol (300 ml) then 1-methyl-4-piperidone (3.73 g, 33 mmol) and the mixture heated at 60° for 5 h, then allowed to stand at ambient temp for 72 h. Evaporation in vacuo gave an orange/red residue which was triturated in dichloromethane and diethyl ether, collected by filtration, washed with diethyl ether and dried in air. Chromatography through silica gel, eluting with ethyl acetate, gave the title compound as a red solid (3.4 g, 59%).

Workup

  1. customEvaporation in vacuo
  2. customgave an orange/red residue which
  3. customwas triturated in dichloromethane
  4. filtrationdiethyl ether, collected by filtration
  5. washwashed with diethyl ether
  6. customdried in air
  7. washChromatography through silica gel, eluting with ethyl acetate

Sources & evidence

ORD record
ord-c289f9d56b254026876f2922a6cf680b
Source dataset
uspto-grants-2001_06
Patent number
US06245778B1

Reaction notes

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