Reaction equation
[CH:1]([C:4]1[C:5]([O:13][CH3:14])=[CH:6][C:7]([CH3:12])=[C:8]([CH:11]=1)[CH:9]=O)([CH3:3])[CH3:2].[C:15]([NH:18][C:19]1[CH:27]=[C:26]2[C:22]([CH2:23][C:24](=[O:28])[NH:25]2)=[CH:21][CH:20]=1)(=[O:17])[CH3:16].N1CCCC1.O>C(O)C>[CH:1]([C:4]1[C:5]([O:13][CH3:14])=[CH:6][C:7]([CH3:12])=[C:8]([CH:11]=1)[CH:9]=[C:23]1[C:22]2[C:26](=[CH:27][C:19]([NH:18][C:15](=[O:17])[CH3:16])=[CH:20][CH:21]=2)[NH:25][C:24]1=[O:28])([CH3:3])[CH3:2]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
A mixture of 5-isopropyl-4-methoxy-2-methylbenzaldehyde (0.25 g, 1.3 mmol), 6-acetamido-2-oxindole (0.25 g, 1.3 mmol) and pyrrolidine (0.54 ml, 6.5 mmol) in ethanol (4 ml) was held in a sealed tube at 100° C. for 12 hours. The reaction was cooled and then poured into water (100 ml). The solid which formed was removed by filtration, washed with water and then dissolved in ethyl acetate (200 ml). The ethyl acetate solution was dried over magnesium sulfate and concentrated. The resulting solid was triturated with dichloromethane/hexanes to afford 0.33 g (70%) of N-[3-(5-isopropyl-4-methoxy-2-methylbenzylidene)-2-oxo-2,3-dihydro-1H-indol-6-yl]-acetamide as a brownish yellow solid.
Workup
- temperatureThe reaction was cooled
- customThe solid which formed
- customwas removed by filtration
- washwashed with water
- dissolutiondissolved in ethyl acetate (200 ml)
- dry with materialThe ethyl acetate solution was dried over magnesium sulfate
- concentrationconcentrated
- customThe resulting solid was triturated with dichloromethane/hexanes
Sources & evidence
- ORD record
- ord-e98db52dd1d24397b55062fec6a0fdab
- Source dataset
- uspto-grants-2005_02
- Patent number
- US06855730B2
Linked notes
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