4-Nitrobenzenesulfonyl chloride → Tert-butyl 1-(4-nitrophenylsulfonyl)-1,2,3,4-tetrahydroquinolin-3-ylcarbamate
Reaction equation
[NH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH:3]([NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])[CH2:2]1.[N+:19]([C:22]1[CH:27]=[CH:26][C:25]([S:28](Cl)(=[O:30])=[O:29])=[CH:24][CH:23]=1)([O-:21])=[O:20].C(N(C(C)C)CC)(C)C>ClCCCl>[N+:19]([C:22]1[CH:23]=[CH:24][C:25]([S:28]([N:1]2[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[CH2:4][CH:3]([NH:11][C:12](=[O:18])[O:13][C:14]([CH3:15])([CH3:17])[CH3:16])[CH2:2]2)(=[O:30])=[O:29])=[CH:26][CH:27]=1)([O-:21])=[O:20]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 75 °C
Procedure
To a solution of tert-butyl 1,2,3,4-tetrahydroquinolin-3-ylcarbamate (3.03 g, 12.2 mmol) and 4-nitrobenzene-1-sulfonyl chloride (2.99 g, 13.5 mmol) in 1,2-dichloroethane (60 mL) was added diisopropylethylamine (6.6 mL, 4.90 g, 37.9 mmol). The mixture was stirred at 75° C. for 15 hours. The mixture was quenched by addition of saturated aqueous sodium bicarbonate (80 mL) and extracted with dichloromethane (3×50 mL). The combined organic layers were washed with water (2×10 mL), dried over anhydrous sodium sulfate and evaporated to dryness. The residue was purified by chromatography on silica gel (30% EtOAc/hexane) to give tert-butyl 1-(4-nitrophenylsulfonyl)-1,2,3,4-tetrahydroquinolin-3-ylcarbamate (4.6 g).
Workup
- customThe mixture was quenched by addition of saturated aqueous sodium bicarbonate (80 mL)
- extractionextracted with dichloromethane (3×50 mL)
- washThe combined organic layers were washed with water (2×10 mL)
- dry with materialdried over anhydrous sodium sulfate
- customevaporated to dryness
- customThe residue was purified by chromatography on silica gel (30% EtOAc/hexane)
Sources & evidence
- ORD record
- ord-d2840152afa545788b65c833b9e9e708
- Source dataset
- uspto-grants-2012_09
- Patent number
- US08273754B2
Reaction notes
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