Reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[NH:9][C:8](=O)[C:7]2=[O:12].[OH-:13].[Na+].C(OCC([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=O)(=O)C.[CH2:34]([OH:36])[CH3:35]>O>[OH:12][C:7]1[C:8]([C:26]2[CH:25]=[CH:24][C:23]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)=[CH:22][CH:27]=2)=[N:9][C:10]2[C:6]([C:35]=1[C:34]([OH:13])=[O:36])=[CH:5][CH:4]=[CH:3][C:2]=2[CH3:1]Participants
Procedure
A suspension of 16.1 g of 7-methyl-2,3-indolinedione in 120 ml of water was treated with a sufficient amount of a solution of 16.6 of sodium hydroxide in 55 ml of water to provide solution. A warm solution of 25.4 g of acetoxyacetylbiphenyl in 350 ml of ethanol was added, followed by the balance of the alkali solution. The mixture was refluxed for 2.5 hours. During the last 1/2 hour 50 ml of ethanol was distilled off. A 300 ml portion of water was added, the mixture was stirred, cooled and filtered through diatomaceous earth. The filtrate was treated with 34 ml of concentrated hydrochloric acid and 12 ml of glacial acetic acid. The resulting solid was collected and recrystallized from ethanol/water, giving 13.6 g of the desired product, mp 178°-180° C.
Workup
- customto provide solution
- temperatureThe mixture was refluxed for 2.5 hours
- distillationDuring the last 1/2 hour 50 ml of ethanol was distilled off
- additionA 300 ml portion of water was added
- temperaturecooled
- filtrationfiltered through diatomaceous earth
- additionThe filtrate was treated with 34 ml of concentrated hydrochloric acid and 12 ml of glacial acetic acid
- customThe resulting solid was collected
- customrecrystallized from ethanol/water
Sources & evidence
- ORD record
- ord-f5040293352c4e43911d9656c29a5a6a
- Source dataset
- uspto-grants-1989_07
- Patent number
- US04847381
Linked notes
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