3-Methoxy-10-nitro-6,11-dihydrodibenzo[b,e]thiepin-11-one → 10-Amino-3-methoxy-6,11-dihydrodibenzo[b,e]thiepin-11-one
Reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[C:12](=[O:13])[C:11]3[C:14]([N+:18]([O-])=O)=[CH:15][CH:16]=[CH:17][C:10]=3[CH2:9][S:8][C:7]=2[CH:21]=1>O.C(O)C.[Fe](Cl)(Cl)Cl>[NH2:18][C:14]1[C:11]2[C:12](=[O:13])[C:6]3[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:21][C:7]=3[S:8][CH2:9][C:10]=2[CH:17]=[CH:16][CH:15]=1Participants
Procedure
In a mixture of water and ethanol (20 ml), 3-methoxy-10-nitro-6,11-dihydrodibenzo[b,e]thiepin-11-one obtained in Reference Example 18 (0.36 g, 1.2 mmol) was heated under reflux in the presence of reduced iron (0.36 g) and iron (III) chloride (40 mg) for 2 hours. After the reaction was completed, the reaction mixture was filtered while hot and the filtrate was evaporated under reduced pressure to give crude 10-amino-3-methoxy-6,11-dihydrodibenzo[b,e]thiepin-11-one (1.2 mmol). This crude product was added without purification to an acid chloride prepared from 3,3,3-trifluoro-2-hydroxy-2-methylpropanoic acid (0.38 g, 2.39 mmol) and thionyl chloride (0.36 ml, 2.39 mmol) in dimethylacetamide (10 ml) in the same manner as in Example 1-48, followed by stirring at room temperature for 6 hours. After the reaction, purification of the reaction product was carried out according to the procedure of Example 1-48 to give Compound 1-49 (0.32 g, yield: 65%).
Workup
- temperaturewas heated
- filtrationthe reaction mixture was filtered while hot and the filtrate
- customwas evaporated under reduced pressure
Sources & evidence
- ORD record
- ord-7a4c51a5c3bd4ddd92ba95f753018e9d
- Source dataset
- uspto-grants-2001_04
- Patent number
- US06211227B1
Reaction notes
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