4-Toluenesulfonyl chloride → 6-Carbomethoxy-8-chloro-5-methoxy-1,2,3,4-tetrahydroquinoline
Reaction equation
O[CH2:2][CH2:3][CH2:4][C:5]1[C:6]([O:17][CH3:18])=[C:7]([CH:12]=[C:13]([Cl:16])[C:14]=1[NH2:15])[C:8]([O:10][CH3:11])=[O:9].C(N(CC)CC)C.S(Cl)(C1C=CC(C)=CC=1)(=O)=O>C(Cl)Cl.C1(C)C=CC=CC=1>[C:8]([C:7]1[C:6]([O:17][CH3:18])=[C:5]2[C:14](=[C:13]([Cl:16])[CH:12]=1)[NH:15][CH2:2][CH2:3][CH2:4]2)([O:10][CH3:11])=[O:9]Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 25 °C
Procedure
A mixture of the compound of step 4 above (1.4 g), triethylamine (1 ml) and TsCl (1.1 g) in CH2Cl2 is stirred at 25° C. for three days. The mixture is washed with saturated aqueous NaHCO3 and evaporated affording a residue which is dissolved in toluene and refluxed for 21/2 hours. The toluene is evaporated and the residue is dissolved in CH2Cl2 and washed with saturated NaHCO3 (25 mls). The organic layer is dried, evaporated and the residue chromatographed on silica gel affording a gum which crystallizes from HexEt2O to give the desired product (M.P. 105°-108° C.).
Workup
- washThe mixture is washed with saturated aqueous NaHCO3
- customevaporated
- customaffording a residue which
- temperaturerefluxed for 21/2 hours
- customThe toluene is evaporated
- dissolutionthe residue is dissolved in CH2Cl2
- washwashed with saturated NaHCO3 (25 mls)
- customThe organic layer is dried
- customevaporated
- customthe residue chromatographed on silica gel affording a gum which
- customcrystallizes from HexEt2O
Sources & evidence
- ORD record
- ord-9d754c7a06e14d3ba3914a8e7d266380
- Source dataset
- uspto-grants-1990_04
- Patent number
- US04920219
Reaction notes
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