Acetic Anhydride → 8-Acetoxy-4-allyloxy-3-methyl-5,6,7,8-tetrahydroquinoline
Reaction equation
[CH2:1]([O:4][C:5]1[C:14]2[CH2:13][CH2:12][CH2:11][CH2:10][C:9]=2[N+:8]([O-])=[CH:7][C:6]=1[CH3:16])[CH:2]=[CH2:3].[C:17]([O:20]C(=O)C)(=[O:19])[CH3:18]>O>[C:17]([O:20][CH:10]1[C:9]2[N:8]=[CH:7][C:6]([CH3:16])=[C:5]([O:4][CH2:1][CH:2]=[CH2:3])[C:14]=2[CH2:13][CH2:12][CH2:11]1)(=[O:19])[CH3:18]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 90 °C
Procedure
To 4.8 g of 4-allyloxy-3-methyl-5,6,7,8-tetrahydroquinoline-N-oxide was added 50 ml of acetic anhydride, and the mixture was stirred at 90° C. for 5 hours. After the reaction was completed, acetic anhydride was removed by evaporation under reduced pressure, to the residue thus obtained was added water and then extracted with chloroform. The chloroform layer was washed with an aqueous solution of sodium hydroxide and an aqueous solution saturated with sodium chloride, then dried with anhydrous magnesium sulfate. Chloroform was removed by evaporation under reduced pressure to obtain 5.0 g of 8-acetoxy-4-allyloxy-3-methyl-5,6,7,8-tetrahydroquinoline in the form of brown oily substance.
Workup
- customacetic anhydride was removed by evaporation under reduced pressure, to the residue
- customthus obtained
- extractionextracted with chloroform
- washThe chloroform layer was washed with an aqueous solution of sodium hydroxide
- dry with materialan aqueous solution saturated with sodium chloride, then dried with anhydrous magnesium sulfate
- customChloroform was removed by evaporation under reduced pressure
Sources & evidence
- ORD record
- ord-868c3e11c46245968f1bc57f73633de2
- Source dataset
- uspto-grants-1989_11
- Patent number
- US04880815
Reaction notes
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