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

HRID 1478400ノート

反応式

HRID 1478400 の反応式
[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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 962Water溶媒

反応条件

温度
85 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-4103865d4a6d4898b4ca94f3ee7daf5f
出典データセット
uspto-grants-2016_08
特許番号
US09403834B2

反応ノート

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