Water → 6-METHYLAMINO-5-NITROQUINOXALINE

HRID 1772008Notes

Reaction equation

C[N:2]([C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[N:12]=[CH:11][CH:10]=[N:9]2)[C:3](=O)C.[N+:16]([O-])([O-:18])=[O:17].[K+].O.[OH-].[Na+]>C(Cl)Cl.S(=O)(=O)(O)O>[CH3:3][NH:2][C:6]1[C:7]([N+:16]([O-:18])=[O:17])=[C:8]2[C:13](=[CH:14][CH:15]=1)[N:12]=[CH:11][CH:10]=[N:9]2

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of N-methyl-N-(quinoxalin-6-yl)acetamide (4.02 g, 0.02 mol) in DCM (60 mL) was added a solution of potassium nitrate (4.02 g, 0.04 mol) in sulfuric acid (10 mL) cooled to 0° C. The mixture was then warmed and stirred at room temperature for 4 h. Water (20 mL) was added. The mixture was adjusted to pH ˜9 with saturated NaOH aqueous solution. Then the mixture was extracted with EtOAc (5×150 mL). The extracts were dried over sodium sulfate and concentrated to give the crude product, which was purified by silica gel column chromatography (eluting with PE/EtOAc v/v 2:1) to give N-methyl-5-nitroquinoxaline-6-amine as a yellow solid (1.4 g, yield 35%). ESI MS: m/z 205.1 [M+H]+. 1H NMR (400 MHz, CDCl3) δ 8.85 (d, J=1.6 Hz, 1H), 8.62 (d, J=1.6 Hz, 1H), 8.07 (d, J=9.6 Hz, 1H), 7.67 (brs, 1H), 7.41 (d, J=9.2 Hz, 1H), 3.18 (s, 3H).

Workup

temperatureThe mixture was then warmed
extractionThen the mixture was extracted with EtOAc (5×150 mL)
dry with materialThe extracts were dried over sodium sulfate
concentrationconcentrated
customto give the crude product, which
customwas purified by silica gel column chromatography (
washeluting with PE/EtOAc v/v 2:1)

Sources & evidence

ORD record: ord-bfc94d455b474c80889f4a2a387fa37b
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09249162B2

Reaction notes

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