Acetic Anhydride → N-(2,3-Dihydro-1H-inden-2-yl)acetamide
Reaction equation
[NH2:1][CH:2]1[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3]1.[C:11](OC(=O)C)(=[O:13])[CH3:12].C(N(CC)CC)C>ClCCl.C(OCC)(=O)C.CCCCCC>[CH2:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[CH2:10][CH:2]1[NH:1][C:11](=[O:13])[CH3:12]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Procedure
2-Aminoindane (1.07 g, 8.03 mmol) was dissolved in dichloromethane (20 ml), and acetic anhydride (0.76 ml, 8.04 mmol) and triethylamine (1.7 ml) were added under ice-cooling, and the mixture was stirred at room temperature for 50 min. The reaction mixture was diluted with ethyl acetate-hexane=1:1 mixed solvent (80 ml), and the organic layer was washed with diluted hydrochloric acid, saturated aqueous sodium hydrogen carbonate and saturated brine and dried over anhydrous magnesium sulfate. The insoluble material was filtered off, and the solution was concentrated under reduced pressure. The obtained solid was washed with diethyl ether-hexane-1:5 mixed solvent, and dried under reduced pressure to give the title compound (961 mg, yield 68%) as a pale-yellow solid.
Workup
- temperaturecooling
- washthe organic layer was washed with diluted hydrochloric acid, saturated aqueous sodium hydrogen carbonate and saturated brine
- dry with materialdried over anhydrous magnesium sulfate
- filtrationThe insoluble material was filtered off
- concentrationthe solution was concentrated under reduced pressure
- washThe obtained solid was washed with diethyl ether-hexane-1:5 mixed solvent
- customdried under reduced pressure
Sources & evidence
- ORD record
- ord-66751d633b93481aa0559fd18da2ed6b
- Source dataset
- uspto-grants-2013_08
- Patent number
- US08513235B2
Reaction notes
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