Nitric Acid → HCID 19696173, compound

HRID 863520Notes

Reaction equation

HRID 863520 reaction equation
[O:1]=[C:2]1[NH:11][C:10]2[C:9]3[CH2:12][CH:13]([C:15]([OH:17])=[O:16])[CH2:14][C:8]=3[CH:7]=[CH:6][C:5]=2[NH:4][C:3]1=[O:18].[N+:19]([O-])([OH:21])=[O:20]>FC(F)(F)C(O)=O>[N+:19]([C:7]1[C:8]2[CH2:14][CH:13]([C:15]([OH:17])=[O:16])[CH2:12][C:9]=2[C:10]2[NH:11][C:2](=[O:1])[C:3](=[O:18])[NH:4][C:5]=2[CH:6]=1)([O-:21])=[O:20]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 19696145HCID 19696145, compound

Product 1

HCID 19696173HCID 19696173, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 2,3-dioxo-2,3,4,7,8,9-hexahydro-1H-cyclopenta[f]quinoxaline-8-carboxylic acid (4 g, 16 mmol) in trifluoroacetic acid (75 mL) was cooled to 0° C. and then treated with fuming nitric acid (5 mL). After stirring in an ice bath for 3 h, the mixture was warmed to room temperature for 1 h, the solvent evaporated, and the residue was suspended in water. A solid precipitate was collected by filtration, washed with ether and dried in vacuo (4 g). Calc'd for C12H9N3 O6.0.5 H2O: C, 48.00; H, 3.36; N, 14.00; found: C, 48.64; H, 3.13; N, 13.86. MS M+1 (292).

Workup

  1. temperaturethe mixture was warmed to room temperature for 1 h
  2. customthe solvent evaporated
  3. filtrationA solid precipitate was collected by filtration
  4. washwashed with ether
  5. customdried in vacuo (4 g)

Sources & evidence

ORD record
ord-178a3e4ad1e844bfab9685ac07bba18f
Source dataset
uspto-grants-1998_02
Patent number
US05721234

Reaction notes

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