Ethanol → 3-Amino-2,3,4,5-tetrahydro-2-oxo-1H-1-benzazepin-1-t-butyl acetate
Reaction equation
C(O)C.[O:4]=[C:5]1[CH:11]([N:12]2C(=O)C3=CC=CC=C3C2=O)[CH2:10][CH2:9][C:8]2[CH:23]=[CH:24][CH:25]=[CH:26][C:7]=2[N:6]1[CH2:27][C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29].O.NN>>[NH2:12][CH:11]1[CH2:10][CH2:9][C:8]2[CH:23]=[CH:24][CH:25]=[CH:26][C:7]=2[N:6]([CH2:27][C:28]([O:30][C:31]([CH3:33])([CH3:32])[CH3:34])=[O:29])[C:5]1=[O:4]Participants
Procedure
To 100 mol of ethanol is added 10 g of tert-butyl 2-oxo-3-phthalimido-2,3,4,5-tetrahydro-1H-1-benzazepine-1-acetate, and 5 g of hydrazine hydrate is added to the mixture, followed by refluxing for 2 hours. The reaction mixture is concentrated under reduced pressure, and 300 ml of water is added to the residue, followed by extraction with 200 ml of ethyl acetate. The extract is washed with 1N aqueous sodium hydroxide and water, successively, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The crystals, which separate out, are treated with a mixture of ether and petroleum ether and collected by filtration to give 6 g of tert-butyl 3-amino-2-oxo-2,3,4,5-tetrahydro-1H-1-benzazepine-1-acetate as colorless prisms. m.p. 121°-122° C.
Workup
- additionis added to the mixture
- temperatureby refluxing for 2 hours
- concentrationThe reaction mixture is concentrated under reduced pressure, and 300 ml of water
- additionis added to the residue
- extractionfollowed by extraction with 200 ml of ethyl acetate
- washThe extract is washed with 1N aqueous sodium hydroxide and water
- dry with materialsuccessively, dried over anhydrous magnesium sulfate
- concentrationconcentrated under reduced pressure
- customThe crystals, which separate out
- additionare treated with a mixture of ether and petroleum ether
- filtrationcollected by filtration
Sources & evidence
- ORD record
- ord-b99ad1c54f5b4a3cb92b43ca78cba541
- Source dataset
- uspto-grants-1989_03
- Patent number
- US04816466
Reaction notes
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