Ethanol → Mosapride
Reaction equation
[Cl:1][C:2]1[C:3]([N+:29]([O-])=O)=[CH:4][C:5]([O:26][CH2:27][CH3:28])=[C:6]([CH:25]=1)[C:7]([NH:9][CH2:10][CH:11]1[O:16][CH2:15][CH2:14][N:13]([CH2:17][C:18]2[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=2)[CH2:12]1)=[O:8].C(O)C>C(OCC)(=O)C>[NH2:29][C:3]1[C:2]([Cl:1])=[CH:25][C:6]([C:7]([NH:9][CH2:10][CH:11]2[O:16][CH2:15][CH2:14][N:13]([CH2:17][C:18]3[CH:19]=[CH:20][C:21]([F:24])=[CH:22][CH:23]=3)[CH2:12]2)=[O:8])=[C:5]([O:26][CH2:27][CH3:28])[CH:4]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 70 °C
Procedure
Stannous chloride dihydrate (5.4 g) is added to a stirred mixture of 5-chloro-2-ethoxy-N-[[4-(4-fluorobenzyl)-2-morpholinyl]methyl]-4-nitrobenzamide (2.2 g), ethanol (30 ml), and ethyl acetate (30 ml). The reaction mixture is stirred at 70° C. for 2 hours and concentrated. The residue is basified with aqueous potassium carbonate solution and extracted with ethyl acetate. The organic layer is washed successively with water and saturated aqueous sodium chloride solution, dried over magnesium sulfate, and evaporated. The residue is recrystallized from ethanol to give the title compound (1.1 g), mp 151°-153° C.