反応式
C(OCC)(=O)C.Cl(O)(=O)(=O)=O.Cl([O-])(=O)(=O)=O.[CH3:17][CH:18]1[CH2:27][C:26]2[CH:25]=[C:24]3[O:28][CH2:29][O:30][C:23]3=[CH:22][C:21]=2[CH:20]([C:31]2[CH:36]=[CH:35][C:34]([N+:37]([O-:39])=[O:38])=[CH:33][CH:32]=2)[OH+:19]1.[NH:40]([C:42]1[N:47]=[CH:46][CH:45]=[CH:44][N:43]=1)[NH2:41]>C(O)(C)C>[N+:37]([C:34]1[CH:35]=[CH:36][C:31]([C:20](=[N:41][NH:40][C:42]2[N:47]=[CH:46][CH:45]=[CH:44][N:43]=2)[C:21]2[C:26]([CH2:27][CH:18]([OH:19])[CH3:17])=[CH:25][C:24]3[O:28][CH2:29][O:30][C:23]=3[CH:22]=2)=[CH:32][CH:33]=1)([O-:39])=[O:38]参加物
反応物 4
生成物 1
試薬・触媒・溶媒 1
実験手順
A stirred mixture of 3.29 g (9.99 mmol) of (±)-7-methyl-5-(4-nitrophenyl)-7,8-dihydro-5H-[1,3]dioxolo[4,5-g]isochroman-5-ol, 40 ml of ethyl acetate and 1.0 ml (1.15 mmol) perchloric acid was refluxed for 1 h. After cooling the precipitated (±)-7-methyl-5-(4-nitrophenyl)-7,8-dihydro-[1,3]dioxolo[4,5-g]isochromen-6-ylium perchlorate was filtered off, and it was stirred at reflux temperature with 1.6 g (14.55 mmol) of 2-hydrazinopyrimdine in 50 ml of isopropanol for 2 h, then concentrated. The residue was dissolved in dichloromethane and washed several times with water. After drying and evaporation the crude product was purified by column chromatography using silica gel (MN Kieselgel 60) as adsorbent and a mixture of toluene-ethyl acetate (0.1:4) as eluent to yield 2.71 g (64%) of the title compound; Mp.: 125-127° C.
後処理
- temperaturewas refluxed for 1 h
- filtrationwas filtered off
- concentrationconcentrated
- dissolutionThe residue was dissolved in dichloromethane
- washwashed several times with water
- customAfter drying
- customevaporation the crude product
- customwas purified by column chromatography
- additiona mixture of toluene-ethyl acetate (0.1:4) as eluent
出典と根拠
- ORDレコード
- ord-7fd80c4ad35640a5957268fc3f7f7d79
- 出典データセット
- uspto-grants-2005_02
- 特許番号
- US06858605B2
関連ノート
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