Ammonia → tert-Butyl 3-nitro-7,8-dihydro-1,6-naphthyridine-6(5H)-carboxylate

HRID 887671Notes

Reaction equation

HRID 887671 reaction equation
N.CO.C[N:5]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[CH:8]=[C:7]([N+]([O-])=O)[C:6]1=O.[C:18]([O:22][C:23]([N:25]1[CH2:30]CC(=O)[CH2:27][CH2:26]1)=[O:24])([CH3:21])([CH3:20])[CH3:19]>>[C:18]([O:22][C:23]([N:25]1[CH2:26][CH2:27][C:6]2[N:5]=[CH:10][C:9]([N+:11]([O-:13])=[O:12])=[CH:8][C:7]=2[CH2:30]1)=[O:24])([CH3:21])([CH3:20])[CH3:19]

Participants

5

Reactant 4

HCID 222AmmoniaHCID 887MethanolHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 36212361-Methyl-3,5-dinitro-1H-pyridin-2-one

Product 1

HCID 10934795tert-Butyl 3-nitro-7,8-dihydro-1,6-naphthyridine-6(5H)-carboxylate

Conditions

Temperature
70 °C

Procedure

2M solution of NH3 in MeOH (225 mL, 452.25 mmol) was added to a reaction vessel containing 1-methyl-3,5-dinitro-1H-pyridin-2-one (6 g, 30.15 mmol) and 4-oxo-piperidine-1-carboxylic acid tert-butyl ester (6.6 g, 33.15 mmol). The vessel was then sealed and the reaction was stirred for 24 h at 70° C. After the resulting mixture was cooled to RT, the solvent was removed to give crude product as yellow solid. After recrystallization in MeOH, the desired title compound was obtained as tan solid. MS (ES+): 280.1 (M+H)+. Calc'd for C13H17N3O4—279.12.

Workup

  1. customThe vessel was then sealed
  2. temperatureAfter the resulting mixture was cooled to RT
  3. customthe solvent was removed
  4. customto give crude product as yellow solid
  5. customAfter recrystallization in MeOH

Sources & evidence

ORD record
ord-5de01793c60d4305949696196f271d3c
Source dataset
uspto-grants-2012_08
Patent number
US08247430B2

Reaction notes

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