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

HRID 1478400노트

반응식

HRID 1478400 반응식
[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

참가 물질

6

반응물 3

HCID 311Citric AcidHCID 14797Potassium HydroxideHCID 90424200methyl 2-(3-phenyl-1H-pyrrole-2-carbonyl)hydrazinecarboxylate

생성물 1

HCID 904249208-Phenyl-2,3-dihydropyrrolo[1,2-d][1,2,4]triazine-1,4-dione수율 88%

시약·촉매·용매 2

HCID 702Ethanol용매HCID 962Water용매

반응 조건

온도
85 °C

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-4103865d4a6d4898b4ca94f3ee7daf5f
출처 데이터셋
uspto-grants-2016_08
특허 번호
US09403834B2

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