HCID 53723761, compound → 6-Nitro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carbonitrile

HRID 276828Notes

Reaction equation

HRID 276828 reaction equation
Cl[C:2]1[C:7]([C:8]([C:10](=[CH:13][N:14](C)C)[C:11]#[N:12])=[O:9])=[CH:6][C:5]([N+:17]([O-:19])=[O:18])=[CH:4][N:3]=1>C(O)C.[OH-].[NH4+]>[N+:17]([C:5]1[CH:6]=[C:7]2[C:2](=[N:3][CH:4]=1)[NH:12][CH:11]=[C:10]([C:13]#[N:14])[C:8]2=[O:9])([O-:19])=[O:18]

Participants

4

Reactant 1

HCID 53723761HCID 53723761, compound

Product 1

HCID 185489506-Nitro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carbonitrileYield 111.9%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 14923Ammonium HydroxideSolvent

Procedure

A solution of 22.4 g (79.8 mmol) of 2-(2-chloro-5-nitro-pyridine-3-carbonyl)-3-dimethylamino-acrylonitrile was refluxed in a mixture of 500 ml of ethanol and 180 ml of conc. ammonium hydroxide for 2 hr. The mixture was cooled and solid was collected which was washed with ether. Concentrating the filtrate gave a second crop which was collected and washed with ether. Solids were combined. After drying, 19.3 g of the title compound was obtained as a yellow solid: mass spectrum (electrospray, m/e): M−H 215 (negative mode).

Workup

  1. temperatureThe mixture was cooled
  2. customsolid was collected which
  3. washwas washed with ether
  4. concentrationConcentrating the filtrate
  5. customgave a second crop which
  6. customwas collected
  7. washwashed with ether
  8. customAfter drying

Sources & evidence

ORD record
ord-8d7adff719d04647a418e0a3a7a0f78d
Source dataset
uspto-grants-2002_03
Patent number
US06355636B1

Reaction notes

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