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

HRID 888091Notes

Reaction equation

HRID 888091 reaction equation
C[N:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[C:4]([N+]([O-])=O)[C:3]1=O.[C:15]([O:19][C:20]([N:22]1[CH2:27]CC(=O)[CH2:24][CH2:23]1)=[O:21])([CH3:18])([CH3:17])[CH3:16].N.CO>>[C:15]([O:19][C:20]([N:22]1[CH2:23][CH2:24][C:3]2[N:2]=[CH:7][C:6]([N+:8]([O-:10])=[O:9])=[CH:5][C:4]=2[CH2:27]1)=[O:21])([CH3:18])([CH3:17])[CH3:16]

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

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.

Workup

  1. customThe solvent was removed
  2. customthe yellow solid was recrystallized from MeOH

Sources & evidence

ORD record
ord-5b015bb9442a4e6f9ebb8855d36ca44c
Source dataset
uspto-grants-2012_08
Patent number
US08247556B2

Reaction notes

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