Thionyl Chloride → HCID 66958491, compound
Reaction equation
[N+:1]([C:4]1[CH:5]=[N:6][C:7]2[C:12]([C:13]=1O)=[CH:11][CH:10]=[CH:9][CH:8]=2)([O-:3])=[O:2].S(Cl)(Cl)=O.[C:19]([O:23][C:24](=[O:30])[NH:25][CH2:26][CH2:27][CH2:28][NH2:29])([CH3:22])([CH3:21])[CH3:20].C(=O)(O)[O-].[Na+]>C(Cl)Cl.CCN(CC)CC.CN(C=O)C>[C:19]([O:23][C:24](=[O:30])[NH:25][CH2:26][CH2:27][CH2:28][NH:29][C:13]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[N:6]=[CH:5][C:4]=1[N+:1]([O-:3])=[O:2])([CH3:22])([CH3:20])[CH3:21]Participants
8
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 0 °C
Procedure
To a stirred solution of 3-nitroquinolin-4-ol (8.15 g) in DCM (100 mL) was added DMF (3.33 mL) and thionyl chloride (3.47 mL) and the reaction mixture was refluxed for 2.5 h when all solids dissolved. The solution was cooled to 0° C. and a solution of (3-aminopropyl)-carbamic acid tert-butyl ester (8.3 g) and Et3N (6.5 mL) in DCM (20 mL) was added dropwise. The reaction mixture was stirred overnight then poured into saturated sodium bicarbonate solution and the product extracted using DCM. The combined organic layer were washed with brine, water, dried, filtered and the solvents evaporated. The residue was trituated with diethylether to leave the subtitle compound (13 g).
Workup
- temperaturethe reaction mixture was refluxed for 2.5 h when all solids
- dissolutiondissolved
- extractionthe product extracted
- washThe combined organic layer were washed with brine, water
- customdried
- filtrationfiltered
- customthe solvents evaporated
Sources & evidence
- ORD record
- ord-7ac4deadcbbc4a14b70feae81fd1753b
- Source dataset
- uspto-grants-2013_05
- Patent number
- US08436178B2
Reaction notes
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