Ethanol → HCID 178473940, compound
Reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)/[C:3](=[CH:10]\[C:11]2[O:15][C:14]([CH:16]=O)=[CH:13][CH:12]=2)/[CH2:2]1.[C:18]([N:21]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH2:23][C:22]1=[O:30])(=[O:20])[CH3:19].N1CCCCC1.C([OH:39])C>>[C:18]([N:21]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)/[C:23](=[CH:16]\[C:14]2[O:15][C:11](/[CH:10]=[C:3]3/[C:2](=[O:39])[NH:1][C:9]4[C:4]/3=[CH:5][CH:6]=[CH:7][CH:8]=4)=[CH:12][CH:13]=2)/[C:22]1=[O:30])(=[O:20])[CH3:19]Participants
Procedure
Diformylfuran (1 equivalent) was dissolved in ethanol, and a solution obtained by dissolving oxindole (0.5 equivalent) and piperidine (0.1 equivalent) in ethanol was gradually added thereto. After completion of the addition, the resulting mixture was stirred at room temperature for 2 hours. After completion of the reaction, the resulting precipitate was removed by filtration. To the filtrate, acetone was added and the resulting solution was acidified with a 1 N hydrochloric acid solution and evaporated to dryness under reduced pressure, whereby 5-((E)-(indolin-3-ylidene)methyl)furan-2-carbaldehyde was obtained (yield: 31%). Subsequently, the thus obtained 5-((E)-(indolin-3-ylidene)methyl)furan-2-carbaldehyde (1.2 equivalents), 1-acetyloxindole (1 equivalent) and piperidine (0.1 equivalent) were dissolved in ethanol and the resulting mixture was stirred at room temperature for 12 hours. After completion of the reaction, the resulting precipitate was collected by filtration, washed with cooled ethanol and dried, whereby a target compound was obtained.
Workup
- customAfter completion of the reaction
- filtrationthe resulting precipitate was collected by filtration
- washwashed with cooled ethanol
- customdried
- customwhereby a target compound was obtained
Sources & evidence
- ORD record
- ord-ab7a24d25c204fb7b1827b99555cdd02
- Source dataset
- uspto-grants-2011_11
- Patent number
- US08053461B2
Reaction notes
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