Sodium Hydroxide → 2-Methyl-8-nitro-1,2,3,4-tetrahydrobenzo[b][1,6]naphthyridine

HRID 585310Notes

Reaction equation

[NH2:1][C:2]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][C:3]=1[CH:4]=O.[CH3:13][N:14]1[CH2:19][CH2:18][C:17](=O)[CH2:16][CH2:15]1.[OH-].[Na+]>C(O)C>[CH3:13][N:14]1[CH2:19][CH2:18][C:17]2[N:1]=[C:2]3[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][C:3]3=[CH:4][C:16]=2[CH2:15]1

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 2-amino-5-nitrobenzaldehyde (1.00 g, 6.02 mmol) and 1-methyl-4-piperidinone (0.89 ml, 7.22 mmol) in ethanol (108 ml) was added a 4N aqueous sodium hydroxide solution (9.0 ml) at room temperature, and the mixture was stirred at 60° C. for 1 hour. The solvent was distilled off under reduced pressure, ethyl acetate was added to the resulting oil, the mixture was washed with an aqueous saturated sodium chloride solution, and dried over anhydrous sodium sulfate. After the solvent was concentrated under reduced pressure, the resulting residue was purified by alumina column chromatography (developing solvent: ethyl acetate), and converted into powders with diisopropyl ether to obtain 2-methyl-8-nitro-1,2,3,4-tetrahydrobenzo[b][1,6]naphthyridine (430 mg).

Workup

distillationThe solvent was distilled off under reduced pressure, ethyl acetate
additionwas added to the resulting oil
washthe mixture was washed with an aqueous saturated sodium chloride solution
dry with materialdried over anhydrous sodium sulfate
concentrationAfter the solvent was concentrated under reduced pressure
customthe resulting residue was purified by alumina column chromatography (developing solvent: ethyl acetate)

Sources & evidence

ORD record: ord-a08e8837baa5475ea756ed3d4ff03b7e
Source dataset: uspto-grants-2005_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06930185B2

Reaction notes

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