Ammonia → HCID 22097122, compound

HRID 1457566Notes

Reaction equation

HRID 1457566 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+].N>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

5

Reactant 3

HCID 222AmmoniaHCID 24434Potassium NitrateHCID 22097136HCID 22097136, compound

Product 1

HCID 22097122HCID 22097122, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
0 °C

Procedure

57.5 g (0.19 mol) of 7-acetamido-1-(ethoxycarbonylmethyl)quinoxaline-2,3(1H,4H)-dione 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 in portions. The cooling was then removed, and the mixture was stirred. After reaction was complete, the mixture was poured into 2 l of ice-water and heated on a waterbath for 2 h. The pH was then adjusted to about 4-5 with aqueous ammonia solution, 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 afford 36.9 g (70%) of product.

Workup

  1. customThe cooling was then removed
  2. customAfter reaction
  3. temperatureheated on a waterbath for 2 h
  4. filtrationthe precipitate was filtered off with suction
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. 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-0c0d4aac79e34be9a124db18751c79ff
Source dataset
uspto-grants-1998_12
Patent number
US05849743

Reaction notes

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