6-Nitroindan-1-one → 6-amino-2,3-dihydro-1H-inden-1-one
Reaction equation
[N+:1]([C:4]1[CH:12]=[C:11]2[C:7]([CH2:8][CH2:9][C:10]2=[O:13])=[CH:6][CH:5]=1)([O-])=O.[H][H]>CCO.[Ni]>[NH2:1][C:4]1[CH:12]=[C:11]2[C:7]([CH2:8][CH2:9][C:10]2=[O:13])=[CH:6][CH:5]=1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Procedure
A mixture of 6-nitroindan-1-one (1 part) and Raney-Ni in EtOH is treated with hydrogen (60 psi) for several hours. The catalyst is removed and the solvent evaporated to give 6-aminoindan-1-one. A solution of the aminoindanone (1 part) in a mixture of pyridine (16 parts), 4-dimethylaminopyridine (0.15 parts), and CH2Cl2 is treated with a solution of an acyl chloride (1.2 parts) and the reaction is stirred overnight. The reaction is poured into ice-water, the organic layer separated and consecutively washed with saturated aqueous sodium bicarbonate and brine. The organics are dried and the solvent evaporated to give the 6-carboxamido-indan-1-one. A solution of this product (1 part) in a mixture of EtOH and NH3 (5 parts) is treated with hydrogen (60 psi) in the presence of Pd--C-sulfided. After several hours, the catalyst is removed and the solvent evaporated to give 1-amino-6-carboxamido-indane. A solution of the indane (1 part) in a mixture of pyridine (16 parts), 4-dimethylaminopyridine (0.15 parts), and CH2Cl2 is treated with a solution of a benzoyl chloride (1.2 parts) and the reaction stirred over night. The reaction is poured into ice-water, the organic layer separated and consecutively washed with saturated aqueous sodium bicarbonate and brine. The organics are dried and the solvent evaporated to give the 1-benzamido-6-carboxamido-indane.
Workup
- customThe catalyst is removed
- customthe solvent evaporated
Sources & evidence
- ORD record
- ord-f6272b2190734161853101ce19315657
- Source dataset
- uspto-grants-2000_07
- Patent number
- US06083986
Reaction notes
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