Nitric Acid → HCID 14985987, compound

HRID 1195682Notes

Reaction equation

Cl.[CH3:2][N:3]1[CH2:8][CH2:7][CH:6]([C:9]2([C:19]([NH2:21])=[O:20])[CH2:17][C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10]2=[O:18])[CH2:5][CH2:4]1.[N+:22]([O-])([OH:24])=[O:23].C(=O)(O)[O-].[Na+]>S(=O)(=O)(O)O>[N+:22]([C:13]1[CH:12]=[C:11]2[C:16]([CH2:17][C:9]([CH:6]3[CH2:7][CH2:8][N:3]([CH3:2])[CH2:4][CH2:5]3)([C:19]([NH2:21])=[O:20])[C:10]2=[O:18])=[CH:15][CH:14]=1)([O-:24])=[O:23]

Participants

Conditions

Temperature: 0 °C

Procedure

To an ice cold solution of 2-(1-methyl-4-piperidyl)-1-oxo-2-indanecarboxamide hydrochloride (5.5 g, 0.0178 mol) in 27 mL of concentrated sulfuric acid was added dropwise over 5 minutes 2.20 g of 90% nitric acid dissolved in 6.8 mL of cold concentrated sulfuric acid. After the addition was complete, the solution was stirred at 0° C. for two hours and then was poured onto ice. The solution was made basic by the addition of solid sodium bicarbonate, and the mixture was extracted with three 100 mL portions of chloroform. The combined chloroform extracts were washed with water, dried over magnesium sulfate, filtered, and the solvent was removed under reduced pressure. The residue was recrystallized from absolute ethanol to give 4.42 g (78% yield)) of 6-nitro-2-(1-methyl-4-piperidyl)-1-oxo-2-indane carboxamide, mp 189°-190° C.

Workup

additionAfter the addition
additionwas poured onto ice
extractionthe mixture was extracted with three 100 mL portions of chloroform
washThe combined chloroform extracts were washed with water
dry with materialdried over magnesium sulfate
filtrationfiltered
customthe solvent was removed under reduced pressure
customThe residue was recrystallized from absolute ethanol

Sources & evidence

ORD record: ord-4df0b6e9d14e4efcb46bed036b45f72b
Source dataset: uspto-grants-1992_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05112824

Reaction notes

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