Ethanol → 4,5,6,7-tetrahydro-2H-isoindol-5-amine
Reaction equation
C([N:4]1[CH:8]=[C:7]2[CH2:9][CH:10]([NH:13]C(=O)C)[CH2:11][CH2:12][C:6]2=[CH:5]1)(=O)C.[OH-].[Na+].C(O)C>O>[CH2:11]1[CH:10]([NH2:13])[CH2:9][C:7]2[C:6](=[CH:5][NH:4][CH:8]=2)[CH2:12]1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
A hydrolysis mixture was prepared from 5.1 g. of dl-2-acetyl-5-acetamido-4,5,6,7-tetrahydro-2H-benzo[c]pyrrole, 50 g. of sodium hydroxide, 50 ml. of water, and 200 ml. of ethanol. The mixture was heated to refluxing temperature under a nitrogen atmosphere for about 16 hours and was then cooled. The cooled mixture was diluted with water. The alkaline aqueous mixture was extracted several times with methylene dichloride, the methylene dichloride extracts were combined and the combined extracts washed with saturated aqueous sodium chloride and dried. Evaporation of the solvent therefrom yielded a residue comprising dl-5-amino-4,5,6,7-tetrahydro-2H-benzo[c]pyrrol formed in the above reaction. A chloroform solution of the residue was filtered through 105 g. of alumina (grade II). Concentration of the resulting filtrate yielded 2.52 g. of a yellow solid comprising dl-5-amino-4,5,6,7-tetrahydro-2H-benzo[c]pyrrole.
Workup
- customA hydrolysis mixture was prepared from 5.1 g
- temperatureThe mixture was heated
- temperatureto refluxing temperature under a nitrogen atmosphere for about 16 hours
- temperaturewas then cooled
- extractionThe alkaline aqueous mixture was extracted several times with methylene dichloride
- washthe combined extracts washed with saturated aqueous sodium chloride
- customdried
- customEvaporation of the solvent
Sources & evidence
- ORD record
- ord-9056ee0ab8f14ad1a0af3f24dcdb678a
- Source dataset
- uspto-grants-1980_11
- Patent number
- US04235776
Reaction notes
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