Acetic Anhydride → 1-Acetylamino-6,7,8,9-tetrahydro-5H-benzocycloheptene
Reaction equation
[N+:1]([C:4]1[C:9]2[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:8]=2[CH:7]=[CH:6][CH:5]=1)([O-])=O.[C:15](OC(=O)C)(=[O:17])[CH3:16]>[Ni].C(O)(=O)C>[C:15]([NH:1][C:4]1[C:9]2[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:8]=2[CH:7]=[CH:6][CH:5]=1)(=[O:17])[CH3:16]Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Procedure
8.7 gm of 1-nitro-6,7,8,9-tetrahydro-5H-benzocycloheptene [J. Am. Chem. Soc., 5820 (9169)] was dissolved into a mixed solvent of 150 ml of acetic anhydride and 50 ml of acetic acid. The mixture was catalytically hydrogenated with the addition of 10 ml of raney nickel. After removing the catalyst by filtration, the reaction mixture was concentrated, the residue was washed with saturated aqueous solution of sodium bicarbonate and saturated brine, and dried over anhydrous sodium sulfate. The product was concentrated to produce 6.17 gm of the title compound.
Workup
- customAfter removing the catalyst
- filtrationby filtration
- concentrationthe reaction mixture was concentrated
- washthe residue was washed with saturated aqueous solution of sodium bicarbonate and saturated brine
- dry with materialdried over anhydrous sodium sulfate
- concentrationThe product was concentrated
Sources & evidence
- ORD record
- ord-691c5df60e61443ba5e4df5ef9964432
- Source dataset
- uspto-grants-1998_06
- Patent number
- US05770605
Reaction notes
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