Piperidine → 5,7-Dimethyl-3-nitro-1,8-naphthyridin-2(1H)-one

HRID 1730648

Reaction equation

HRID 1730648 reaction equation
[NH2:1][C:2]1[N:9]=[C:8]([CH3:10])[CH:7]=[C:6]([CH3:11])[C:3]=1[CH:4]=O.[N+:12]([CH2:15][C:16](OCC)=[O:17])([O-:14])=[O:13].N1CCCCC1>C(O)C>[N+:12]([C:15]1[C:16](=[O:17])[NH:1][C:2]2[C:3]([CH:4]=1)=[C:6]([CH3:11])[CH:7]=[C:8]([CH3:10])[N:9]=2)([O-:14])=[O:13]

Participants

5

Reactant 3

HCID 8082PiperidineHCID 69379Ethyl nitroacetateHCID 123666092-Amino-4,6-dimethylpyridine-3-carbaldehyde

Product 1

HCID 214960955,7-Dimethyl-3-nitro-1,8-naphthyridin-2(1H)-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-amino-4,6-dimethylnicotinaldehyde (2.40 g., 16 mmole), ethyl nitroacetate (5.12 g., 32 mmole), piperidine (336 mg., 4 mmole) and ethanol (4 ml.) is heated under reflux with stirring for an hour. The mixture then is cooled, treated with petroleum ether, the solid removed by filtration and recrystallized from methanol yielding 1.55 g. (44%) of product, m.p. 270°-272° C. (dec.). Following recrystallization from the same solvent the product melts at 272°- 274° C. (dec.).

Workup

  1. temperatureis heated
  2. temperatureunder reflux
  3. temperatureThe mixture then is cooled
  4. customthe solid removed by filtration
  5. customrecrystallized from methanol yielding 1.55 g
  6. customrecrystallization from the same solvent the product melts at 272°- 274° C. (dec.)

Sources & evidence

ORD record
ord-e01b5492b4c64ee18caa3333c7543f5d
Source dataset
uspto-grants-1976_11
Patent number
US03993656

Linked notes

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