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

HRID 1066765Notes

Reaction equation

HRID 1066765 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.CO.[CH2:18]([N:25]1[CH2:30]CC(=O)[CH2:27][CH2:26]1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>>[CH2:18]([N:25]1[CH2:26][CH2:27][C:5]2[N:6]=[CH:7][C:8]([N+:10]([O-:12])=[O:11])=[CH:9][C:4]=2[CH2:30]1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 4

HCID 222AmmoniaHCID 887MethanolHCID 192201-Benzyl-4-piperidoneHCID 36212361-Methyl-3,5-dinitro-1H-pyridin-2-one

Product 1

HCID 114371286-Benzyl-3-nitro-5,6,7,8-tetrahydro-1,6-naphthyridineYield 93%

Conditions

Temperature
60 °C

Procedure

3,5-Dinitro-1-methyl-2-pyridone (1.99 g; 10 mmol) [prepared according to E. Matsumura, M. Ariga and Y. Tohda, Bull. Chem. Soc. Japan, 1979, 52, 2413 ] was added to a solution of ammonia in methanol (1.1M; 100 ml; 110 mmol) and then treated with 1-benzyl-4-piperidone (2.27 g; 12 mmol). The resulting mixture was heated at 60° C. for 5 h, cooled to room temperature and evaporated to dryness in vacuo. The residue was purified by chromatography through SiO2 eluting with 50% ethyl acetate/60-80° pet. ether to give the title compound (2.5 g; 93%). Recrystallisation from ethyl acetate −60-80° petroleum ether gave the title compound as a pale yellow, microcrystalline solid, mp 108° C.

Workup

  1. temperaturecooled to room temperature
  2. customevaporated to dryness in vacuo
  3. customThe residue was purified by chromatography through SiO2 eluting with 50% ethyl acetate/60-80° pet. ether

Sources & evidence

ORD record
ord-293891aa8291497fb5a2ef79c661069b
Source dataset
uspto-grants-2001_06
Patent number
US06245778B1

Reaction notes

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