Nitric Acid → 9-Amino-6-nitro-1,4,7,8,9,10-hexahydro-benzo[f]quinoxaline-2,3-dione

HRID 863488Notes

Reaction equation

[NH2:1][CH:2]1[CH2:17][C:6]2[C:7]3[NH:8][C:9](=[O:16])[C:10](=[O:15])[NH:11][C:12]=3[CH:13]=[CH:14][C:5]=2[CH2:4][CH2:3]1.[N+:18]([O-])([OH:20])=[O:19]>FC(F)(F)C(O)=O>[NH2:1][CH:2]1[CH2:17][C:6]2[C:7]3[NH:8][C:9](=[O:16])[C:10](=[O:15])[NH:11][C:12]=3[CH:13]=[C:14]([N+:18]([O-:20])=[O:19])[C:5]=2[CH2:4][CH2:3]1

Participants

Conditions

Temperature: 0 °C

Procedure

A mixture of 9-amino-1,4,7,8,9,10-hexahydrobenzo[f]quinoxaline-2,3-dione and trifluoroacetic acid (10 mL) was cooled in an ice bath and then treated with fuming nitric acid (0.5 mL) and stirred for 3 h at 0° C. and then 1 h at room temperature. After removing the solvent by rotoevaporation, the residue was triturated with acetone and the resulting solid collected by filtration to give the product (0.22 g, 93% yield). The solid was stirred in 2N HCl for 15 min, collected by filtration and dried to give the hydrochloride salt. Anal. calc'd for C12H12N4O4.HCl.H2O--C, 43.58; H, 4.57; N, 16.94; found -C, 43.56; H, 4.08; N, 16.51.

Workup

temperaturewas cooled in an ice bath
custom1 h
customat room temperature
customAfter removing the solvent by rotoevaporation
customthe residue was triturated with acetone
filtrationthe resulting solid collected by filtration

Sources & evidence

ORD record: ord-8c65e16497464e56bac89c2c27a97e7f
Source dataset: uspto-grants-1998_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05721234

Reaction notes

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