Potassium Nitrate → HCID 22097122, compound

HRID 1458867Notes

Reaction equation

C([NH:4][C:5]1[CH:14]=[C:13]2[C:8]([NH:9][C:10](=[O:22])[C:11](=[O:21])[N:12]2[CH2:15][C:16]([O:18]CC)=[O:17])=[CH:7][CH:6]=1)(=O)C.[N+:23]([O-])([O-:25])=[O:24].[K+]>S(=O)(=O)(O)O>[NH2:4][C:5]1[CH:14]=[C:13]2[C:8]([NH:9][C:10](=[O:22])[C:11](=[O:21])[N:12]2[CH2:15][C:16]([OH:18])=[O:17])=[CH:7][C:6]=1[N+:23]([O-:25])=[O:24]

Participants

Conditions

Temperature: 0 °C

Procedure

57.5 g (0.19 mol) of 7-acetamido-1-(ethoxycarbonylmethyl)-2,3(1H,4H)-quinoxalinedione were dissolved in 575 ml of concentrated sulfuric acid. The solution was cooled to 0° C., and 19.0 g (0.19 mol) of potassium nitrate were added a little at a time. The cooling was then removed and the mixture was stirred until the reaction was complete and was then poured into 2 l of ice-water and heated on a water bath for 2 h. The pH was then adjusted with aqueous ammonia solution to about 4-5, and the precipitate was filtered off with suction. The filtrate was concentrated under reduced pressure, and the residue was purified by chromatography on silica gel (mobile phase: methanol/tetrahydrofuran/water==5:4:1+2.5% glacial acetic acid). The resulting product was combined with the first precipitate to yield 36.9 g (70%) of product.

Workup

customThe cooling was then removed
additionwas then poured into 2 l of ice-water
temperatureheated on a water bath for 2 h
filtrationthe precipitate was filtered off with suction
concentrationThe filtrate was concentrated under reduced pressure
customthe residue was purified by chromatography on silica gel (mobile phase: methanol/tetrahydrofuran/water==5:4:1+2.5% glacial acetic acid)

Sources & evidence

ORD record: ord-b3b5da196dbd4017bc0a6e9547247f0f
Source dataset: uspto-grants-1998_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05852017

Reaction notes

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