Methanol → Methyl 7-bromo-2,3-dihydro-1H-1-benzazepine-4-carboxylate
Reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:11][CH2:10][CH2:9][C:8]([C:12]([OH:14])=[O:13])=[CH:7][C:6]=2[CH:15]=1.S(=O)(=O)(O)O.[CH3:21]O>>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:11][CH2:10][CH2:9][C:8]([C:12]([O:14][CH3:21])=[O:13])=[CH:7][C:6]=2[CH:15]=1Participants
Conditions
- Temperature
- 80 °C
Procedure
To a suspension of 7-bromo-2,3-dihydro-1-benzazepine-4-carboxylic acid (68.2 g) in methanol (100 ml) was added concentrated sulfuric acid (37.3 g) at 0° C., and the mixture was heated at 80° C. for 10 hours. After allowing to cool, the solvent was evaporated under reduced pressure. Ethyl acetate and water were added thereto and 1N sodium hydroxide solution was added to pH=4 at 0° C. The solution was separated, and the organic phase was washed with water and saturated brine and dried with magnesium sulfate. The solvent was evaporated under reduced pressure, the resulting residue was subjected to silica gel column to remove origin components (ethyl acetate), and the resulting solid was washed with diisopropyl ether to give methyl 7-bromo-2,3-dihydro-1-benzazepine-4-carboxylate (44.0 g). The filtrate was purified with silica gel column (hexane:ethyl acetate=4:1) to give methyl 7-bromo-2,3-dihydro-1-benzazepine-4-carboxylate (3.4 g).
Workup
- temperatureto cool
- customthe solvent was evaporated under reduced pressure
- additionEthyl acetate and water were added
- addition1N sodium hydroxide solution was added to pH=4 at 0° C
- customThe solution was separated
- washthe organic phase was washed with water and saturated brine
- dry with materialdried with magnesium sulfate
- customThe solvent was evaporated under reduced pressure
- customto remove origin components (ethyl acetate)
- washthe resulting solid was washed with diisopropyl ether
Sources & evidence
- ORD record
- ord-d8c4bf63a7014b589e736986389a0c6c
- Source dataset
- uspto-grants-2005_08
- Patent number
- US06936602B1
Reaction notes
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