Sodium Hydroxide → HCID 12789224, compound
Reaction equation
[CH3:1][O:2][C:3]1[C:13]([O:14][CH3:15])=[CH:12][C:6]2[CH2:7][CH2:8][NH:9][CH2:10][CH2:11][C:5]=2[CH:4]=1.[Br:16]Br.[OH-].[Na+]>C(O)(=O)C>[Br:16][C:4]1[C:5]2[CH2:11][CH2:10][NH:9][CH2:8][CH2:7][C:6]=2[CH:12]=[C:13]([O:14][CH3:15])[C:3]=1[O:2][CH3:1]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 70 °C
Procedure
To a solution of 12.8 g. (0.052 mole) of 7,8-dimethoxy-2,3,4,5-tetrahydro-1H-3-benzazepine (prepared as in Example 1) in 50 ml. of glacial acetic acid at 55° C. was added 3.0 ml. of bromine (8.8 g., 0.055 mole) dropwise over 1 hour with stirring. After addition was completed, the temperature was raised to 70° C. for 2 hours. The reaction mixture was poured into ice/water and made basic with 40% sodium hydroxide solution. The basic solution was extracted with ethyl acetate and the extract dried over sodium sulfate. Removal of the solvent gave 6-bromo-7,8-dimethoxy-2,3,4,5-tetrahydro-1H-3-benzazepine as an oil.
Workup
- additionAfter addition
- extractionThe basic solution was extracted with ethyl acetate
- dry with materialthe extract dried over sodium sulfate
- customRemoval of the solvent
Sources & evidence
- ORD record
- ord-5ee5fa8dc9d34a65ab9921be6e3b33f2
- Source dataset
- uspto-grants-1981_05
- Patent number
- US04265890
Reaction notes
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