Hydrochloric Acid → N-(2,3-Dihydro-1H-inden-5-yl)acetamide
Reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[CH2:7][CH2:6][CH2:5]2.C(N(CC)CC)C.[C:18](OC(=O)C)(=[O:20])[CH3:19].Cl>C(Cl)Cl>[C:18]([NH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[CH2:7][CH2:6][CH2:5]2)(=[O:20])[CH3:19]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 7.18 g (54 mmol) of 5-aminoindane and 10.9 g (108 mmol) of triethylamine in 40 mL of CH2Cl2 is cooled to 5° C. Acetic anhydride (7.63 g, 81 mmol) is added carefully dropwise. The reaction is allowed to warm to room temperature and stirred overnight. The reaction is poured into 1 N HCl to acidify it and is then extracted with EtOAc. The organic layer is evaporated in vacuo. Toluene is added to the residue and the mixture is evaporated in vacuo to give 5-acetylaminoindane that was used without purification. 5-Acetylaminoindane (8.8 g) is dissolved in a solution of 26 mL of HOAc and 126 mL of acetic anhydride, and cooled to 0° C. Nitric acid (8.3 mL) is added carefully dropwise to the solution so as to control the temperature of the exothermic reaction. The mixture is stirred for an additional 30 minutes and is poured onto ice and filtered. The solid is washed with water and dried in a vacuum oven overnight to give 5-acetylamino-6-nitroindane that is used without further purification. A mixture of this solid in 230 mL of 6 N HCl is heated to reflux for 4 hours. The mixture is neutralized with Na2CO3 (152 g) in 1000 mL of H2O. The solids are filtered and dried overnight in a vacuum oven to give 5-amino-6-nitroindane.
Workup
- extractionis then extracted with EtOAc
- customThe organic layer is evaporated in vacuo
- additionToluene is added to the residue
- customthe mixture is evaporated in vacuo
Sources & evidence
- ORD record
- ord-6bad118e27cd423e955c92862744c897
- Source dataset
- uspto-grants-2007_04
- Patent number
- US07202364B2
Reaction notes
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