Reaction equation
Cl.[CH2:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][NH:3]1.[OH-].[Na+].[N+:13]([C:16]1[CH:17]=[C:18]([CH:23]=[CH:24][CH:25]=1)[CH:19]=[CH:20][CH2:21][Cl:22])([O-:15])=[O:14]>O.C(O)C>[ClH:22].[N+:13]([C:16]1[CH:17]=[C:18]([CH:23]=[CH:24][CH:25]=1)[CH:19]=[CH:20][CH2:21][N:3]1[CH2:4][C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH2:2]1)([O-:15])=[O:14]Participants
Procedure
The process for the preparation of this compound and its physical properties will be given below. A solution of 5.68 grams of isoindoline hydrochloride and 2.86 grams of sodium hydroxide in 15 milliliters of water is added to a solution of 6.8 grams of m-nitrocinnamyl chloride in 160 milliliters of ethanol, and the mixture is stirred for 10 hours at room temperature. After completion of the reaction, the reaction product is concentrated, and the residue is extracted with chloroform. The extract is then purified by silica gel column chromatography, following which the resulting oily product is converted to a hydrochloride in a customary manner and recrystallized from ethanol to obtain 5.6 grams (yield 52%) of N-(m-nitrocinnamyl)-isoindoline hydrochloride as crystals having a melting point of 208°-210° C. (decomposition).
Workup
- customThe process for the preparation of this compound and its physical properties
- customAfter completion of the reaction
- concentrationthe reaction product is concentrated
- extractionthe residue is extracted with chloroform
- customThe extract is then purified by silica gel column chromatography
- customrecrystallized from ethanol
Sources & evidence
- ORD record
- ord-0cb01a295cd8484ba4fc4671b7de70c3
- Source dataset
- uspto-grants-1978_09
- Patent number
- US04115398
Linked notes
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