Nitric Acid → HCID 118080532, compound

HRID 1485780Notes

Reaction equation

HRID 1485780 reaction equation
[C:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([Br:14])=[CH:11][CH:12]=2)[N:7]([C:15]([O:17][CH:18]([CH3:20])[CH3:19])=[O:16])[CH2:6][C@@H:5]1[CH3:21])(=[O:3])[CH3:2].[N+:22]([O-])([OH:24])=[O:23]>C(O)(=O)C>[C:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([Br:14])=[C:11]([N+:22]([O-:24])=[O:23])[CH:12]=2)[N:7]([C:15]([O:17][CH:18]([CH3:20])[CH3:19])=[O:16])[CH2:6][C@@H:5]1[CH3:21])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 118079263HCID 118079263, compound

Product 1

HCID 118080532HCID 118080532, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
110 °C

Procedure

A reaction vial was charged with isopropyl (S)-4-acetyl-7-bromo-3-methyl-3,4-dihydroquinoxaline-1(2H)-carboxylate (0.100 g, 0.282 mmol) and acetic acid (1 mL), and the reaction was heated to 110° C. Nitric acid (37.7 μL, 0.845 mmol) was added dropwise and the reaction was stirred at 110° C. for 1 h. The reaction was cooled to ambient temperature and then added dropwise to an ice/water bath. The resulting slurry was filtered, and the filter cake was dried overnight under vacuum to provide isopropyl (S)-4-acetyl-7-bromo-3-methyl-6-nitro-3,4-dihydroquinoxaline-1(2H)-carboxylate (0.111 g, 99%) as a white solid. MS (ESI, pos. ion) m/z 428 [M+H]+.

Workup

  1. customA reaction
  2. temperatureThe reaction was cooled to ambient temperature
  3. additionadded dropwise to an ice/water bath
  4. filtrationThe resulting slurry was filtered
  5. customthe filter cake was dried overnight under vacuum

Sources & evidence

ORD record
ord-66efca08ef9d419294cc342858622c7b
Source dataset
uspto-grants-2016_08
Patent number
US09422281B2

Reaction notes

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