4-Amino-2-nitrobenzoic Acid → 4-(6-Bromo-4-methyl-3-oxo-3,4-dihydro-pyrazin-2-ylamino)-2-nitro-benzoic acid

HRID 551863

Reaction equation

Br[C:2]1[C:3](=[O:10])[N:4]([CH3:9])[CH:5]=[C:6]([Br:8])[N:7]=1.[NH2:11][C:12]1[CH:20]=[CH:19][C:15]([C:16]([OH:18])=[O:17])=[C:14]([N+:21]([O-:23])=[O:22])[CH:13]=1>C(O)(C)C>[Br:8][C:6]1[N:7]=[C:2]([NH:11][C:12]2[CH:20]=[CH:19][C:15]([C:16]([OH:18])=[O:17])=[C:14]([N+:21]([O-:23])=[O:22])[CH:13]=2)[C:3](=[O:10])[N:4]([CH3:9])[CH:5]=1

Participants

Conditions

Temperature: 90 °C

Procedure

3,5-Dibromo-1-methyl-1H-pyrazin-2-one (1.0 g, 3.73 mmol) and 4-amino-2-nitrobenzoic acid (0.68 g, 3.73 mmol) are dissolved in isopropanol (20 mL) and heated at 90° C. for 4 hours. The reaction is cooled to room temperature and the resulting suspension is filtered. The filter cake is then washed with ethyl ether (3×100 mL) and air dried to give 4-(6-bromo-4-methyl-3-oxo-3,4-dihydro-pyrazin-2-ylamino)-2-nitro-benzoic acid (3) as a tan solid (1.17 g).

Workup

temperatureThe reaction is cooled to room temperature
filtrationthe resulting suspension is filtered
washThe filter cake is then washed with ethyl ether (3×100 mL) and air
customdried

Sources & evidence

ORD record: ord-22bb9fd884da49898b420edd49da3444
Source dataset: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07947835B2

Linked notes

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