Nitric Acid → HCID 19696166, compound

HRID 863497Notes

Reaction equation

HRID 863497 reaction equation
[Br:1][C:2]1[C:11]2[NH:10][C:9](=[O:12])[C:8](=[O:13])[NH:7][C:6]=2[C:5]2[CH2:14][CH:15]([NH:17][C:18](=[O:20])[CH3:19])[CH2:16][C:4]=2[CH:3]=1.[N+:21]([O-])([OH:23])=[O:22]>FC(F)(F)C(O)=O>[Br:1][C:2]1[C:11]2[NH:10][C:9](=[O:12])[C:8](=[O:13])[NH:7][C:6]=2[C:5]2[CH2:14][CH:15]([NH:17][C:18](=[O:20])[CH3:19])[CH2:16][C:4]=2[C:3]=1[N+:21]([O-:23])=[O:22]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 19696197HCID 19696197, compound

Product 1

HCID 19696166HCID 19696166, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
0 °C

Procedure

N-(5-Bromo-2,3-dioxo-2,3,4,7,8,9-hexahydro-1H-cyclopenta[f]quinoxalin-8-yl)-acetamide (0.24 g, 0.7 mmol) was dissolved in trifluoroacetic acid (10 mL), cooled in an ice bath to 0° C., and then treated with fuming nitric acid (0.5 mL) and stirred for 4 h at 0° C. After removing the solvent by rotoevaporation, the syrupy residue was triturated with water and the resulting solid was collected by filtration, washed with water and then ether and dried in vacuo (0.22 g, 81% yield). Anal. calc'd for C13H11BrN4O5.H2O: C, 38.92; H, 3.27; N, 13.94. Found: C, 38.60; H, 3.00; N, 13.66.

Workup

  1. customAfter removing the solvent by rotoevaporation
  2. customthe syrupy residue was triturated with water
  3. filtrationthe resulting solid was collected by filtration
  4. washwashed with water
  5. dry with materialether and dried in vacuo (0.22 g, 81% yield)

Sources & evidence

ORD record
ord-8a9f21bbe0fb403ea3d73bf58b32fe09
Source dataset
uspto-grants-1998_02
Patent number
US05721234

Reaction notes

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