HCID 13417979, compound → 2,3-Dihydro-2-(2,2-diethoxyethyl)-3-(1-aminoethyl)-isoindol-1-one
Reaction equation
[CH2:1]([O:3][CH:4]([O:21][CH2:22][CH3:23])[CH2:5][N:6]1[CH:14]([CH:15]([N+:17]([O-])=O)[CH3:16])[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]1=[O:20])[CH3:2]>[Pd].C(O)(=O)C.O>[CH2:22]([O:21][CH:4]([O:3][CH2:1][CH3:2])[CH2:5][N:6]1[CH:14]([CH:15]([NH2:17])[CH3:16])[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]1=[O:20])[CH3:23]Participants
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 25 °C
Procedure
A mixture of the two isomers of 2,3-dihydro-2-(2,2-diethoxyethyl)-3-(1-nitroethyl)-isoindol-1-one (2.5 g, described in Example 30) and 10% palladium on carbon (0.25 g) in acetic acid-water (4:1, 50 ml) is stirred under an atmosphere of hydrogen at 50 psi and 25° C. for 18 hr and filtered. The filtrate is evaporated and dissolved in 2% hydrochloric acid. The solution is washed with diethyl ether, basified to pH 9 with ammonium hydroxide and extracted with ethyl acetate. The organic extract is dried, evaporated and chromatographed on silica gel using acetone-benzene (2:3). Evaporation of the eluates gives isomer A (1.14 g) of the title compound, ir (CHCl3) 1675, 1120 and 1050 cm-1 and isomer B (0.88 g) of the title compound, ir (CHCl3) 1675, 1120 and 1050 cm-1.
Workup
- filtrationfiltered
- customThe filtrate is evaporated
- dissolutiondissolved in 2% hydrochloric acid
- washThe solution is washed with diethyl ether
- extractionextracted with ethyl acetate
- extractionThe organic extract
- customis dried
- customevaporated
- customchromatographed on silica gel
- customEvaporation of the eluates
Sources & evidence
- ORD record
- ord-3a905846430242ef88e400831f973ddc
- Source dataset
- uspto-grants-1981_06
- Patent number
- US04273773
Reaction notes
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