Aminoacetaldehyde dimethyl acetal → HCID 23462902, compound
Reaction equation
[F:1][C:2]1[C:11]([O:12][CH3:13])=[C:10]([O:14][CH3:15])[CH:9]=[CH:8][C:3]=1[CH2:4][C:5]([OH:7])=O.[CH3:16][O:17][CH:18]([O:21][CH3:22])[CH2:19][NH2:20]>>[CH3:16][O:17][CH:18]([O:21][CH3:22])[CH2:19][NH:20][C:5](=[O:7])[CH2:4][C:3]1[CH:8]=[CH:9][C:10]([O:14][CH3:15])=[C:11]([O:12][CH3:13])[C:2]=1[F:1]Participants
Procedure
Following the procedures outlined in Examples 1 and 2, the 2-fluorohomoveratric acid is reacted with aminoacetaldehyde dimethylacetal to form N-(2,2-dimethoxyethyl)-3,4,-dimethoxy-2-fluorophenylacetamide which is ring closed with hydrochloric acid and glacial acetic acid to obtain 2,3-dihydro-7,8-dimethoxy-6-fluoro-2-oxo-1H-3-benzazepine. The dihydrobenzazepine is reduced first with hydrogen and palladium-on-carbon, then with diborane to give 7,8-dimethoxy-6-fluoro-2,3,4,5-tetrahydro-1H-3-benzazepine. The latter is treated with formaldehyde/formic acid to give the corresponding 3-methyl derivative which is demethylated with 48% hydrobromic acid. The resulting catechol is oxidized with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone and the dione is treated with a methanolic solution of thiophenol to furnish the product 7,8-dihydroxy-9-fluoro-3-methyl-6-phenyl-thio-2,3,4,5-tetrahydro-1H-3-benzazepine.
Sources & evidence
- ORD record
- ord-bf9ff1a60dd84e5fb711710b3d01691d
- Source dataset
- uspto-grants-1981_05
- Patent number
- US04265890
Reaction notes
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