Ethanol → 5-({7-[3-(Diethylamino)propoxy]-6-methoxy-4-quinolyl}sulfanyl)-2-thiopheneamine
Reaction equation
[CH2:1]([N:3]([CH2:29][CH3:30])[CH2:4][CH2:5][CH2:6][O:7][C:8]1[CH:17]=[C:16]2[C:11]([C:12]([S:18][C:19]3[S:20][C:21]([N+:24]([O-])=O)=[CH:22][CH:23]=3)=[CH:13][CH:14]=[N:15]2)=[CH:10][C:9]=1[O:27][CH3:28])[CH3:2].[Cl-].[NH4+].C(O)C>[Fe].O>[CH2:29]([N:3]([CH2:1][CH3:2])[CH2:4][CH2:5][CH2:6][O:7][C:8]1[CH:17]=[C:16]2[C:11]([C:12]([S:18][C:19]3[S:20][C:21]([NH2:24])=[CH:22][CH:23]=3)=[CH:13][CH:14]=[N:15]2)=[CH:10][C:9]=1[O:27][CH3:28])[CH3:30]Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Procedure
N,N-Diethyl-N-[3-((6-methoxy-4-[(5-nitro-2-thienyl)sulfanyl]-7-quinolyl)oxy)propyl]amine (525 mg), iron powder (330 mg), ammonium chloride (660 mg), ethanol (20 ml) and water (5 ml) were stirred together at 80° C. for 80 minutes. After filtration with celite, NH type silica gel was added to the filtrate, the solvent was distilled off under reduced pressure and the reaction product was adsorbed onto the silica gel. The silica gel was charged into a dry column packed with NH type silica gel, and column purification was performed (ethyl acetate, followed by ethyl acetate:methanol=3:1) to obtain 190 mg of a brown oil.
Workup
- filtrationAfter filtration with celite, NH type silica gel
- additionwas added to the filtrate
- distillationthe solvent was distilled off under reduced pressure
- additionThe silica gel was charged into a dry column
- custompacked with NH type silica gel, and column purification
Sources & evidence
- ORD record
- ord-4a969991937b4b13a0bc2601c8fe4a74
- Source dataset
- uspto-grants-2009_11
- Patent number
- US07612092B2
Reaction notes
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