Reacción #975273

ord-5b015bb9442a4e6f9ebb8855d36ca44c

Ecuación de reacción

Cn1cc([N+](=O)[O-])cc([N+](=O)[O-])c1=O
1-Methyl-3,5-dinitro-1H-pyridin-2-one
CC(C)(C)OC(=O)N1CCC(=O)CC1
4-oxo-piperidine-1-carboxylic acid tert-butyl ester
N
NH3
CO
MeOH
→
CC(C)(C)OC(=O)N1CCc2ncc([N+](=O)[O-])cc2C1
3-nitro-7,8-dihydro-5H-[1,6]naphthyridine-6-carboxylic acid tert-butyl ester

Reactantes

Cn1cc([N+](=O)[O-])cc([N+](=O)[O-])c1=O
1-Methyl-3,5-dinitro-1H-pyridin-2-one
CC(C)(C)OC(=O)N1CCC(=O)CC1
4-oxo-piperidine-1-carboxylic acid tert-butyl ester
N
NH3
CO
MeOH
—
solution

Reactivos

Ninguno

Condiciones de reacción

Temperatura
70°CELSIUS
Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    OtroThe solvent was removed
  2. 2
    Otrothe yellow solid was recrystallized from MeOH

Procedimiento

1-Methyl-3,5-dinitro-1H-pyridin-2-one (6.0 g, 30.15 mmol), and 4-oxo-piperidine-1-carboxylic acid tert-butyl ester (6.6 g, 33.15 mmol) were added to a 2 M solution of NH3 in MeOH (225 mL, 452.3 mmol) in a sealed tube. The reaction was heated to 70° C. for 16 h. The solvent was removed and the yellow solid was recrystallized from MeOH affording 3-nitro-7,8-dihydro-5H-[1,6]naphthyridine-6-carboxylic acid tert-butyl ester as tan solid.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US08247556B2uspto-grants-2012_08