Citric Acid → 8-Phenyl-2,3-dihydropyrrolo[1,2-d][1,2,4]triazine-1,4-dione

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Reaktionsgleichung

[C:1]1([C:7]2[CH:11]=[CH:10][NH:9][C:8]=2[C:12]([NH:14][NH:15][C:16]([O:18]C)=O)=[O:13])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[K+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C(O)C.O>[C:1]1([C:7]2[CH:11]=[CH:10][N:9]3[C:8]=2[C:12](=[O:13])[NH:14][NH:15][C:16]3=[O:18])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Komponenten

Reaktionsbedingungen

Temperatur: 85 °C

Versuchsvorschrift

To a solution of methyl 2-(3-phenyl-1H-pyrrole-2-carbonyl)hydrazinecarboxylate (4.00 g, 15.0 mmol) in ethanol (60 mL) was added potassium hydroxide (4.33 g, 770 mmol) at room temperature and heated to 85° C. for 30 min. The reaction mixture was evaporated under reduced pressure to give a brown solid, which was redissolved in water (100 mL) and acidified with saturated citric acid solution to pH 7. The solid obtained was filtered through the Buchner funnel and further it was triturated with hexane to yield 8-phenyl-2,3-dihydropyrrolo[1,2-d][1,2,4]triazine-1,4-dione (3.00 g, 86.0%) as a white solid. LCMS method B-3: retention time 1.59 min, [M+1]=228.0. 1H NMR (400 MHz, DMSO-d6) δ ppm: 6.88 (d, J=2.8 Hz, 1H), 7.29-7.39 (m, 3H), 7.64-7.66 (m, 2H), 7.76 (d, J=2.8 Hz, 1H), 11.43 (br s, 2H).

Aufarbeitung

customThe reaction mixture was evaporated under reduced pressure
customto give a brown solid, which
customThe solid obtained
filtrationwas filtered through the Buchner funnel and further it
customwas triturated with hexane

Quellen und Nachweise

ORD-Eintrag: ord-4103865d4a6d4898b4ca94f3ee7daf5f
Quelldatensatz: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US09403834B2

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