Reaction equation
[Cl:1][C:2]1[C:11]([C:12]([OH:14])=O)=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.CCN(CC)CC.[S:22]1[CH:26]=[CH:25][CH:24]=[C:23]1[CH2:27][NH2:28].CCCCCC>S(Cl)(Cl)=O>[Cl:1][C:2]1[C:11]([C:12]([NH:28][CH2:27][C:23]2[S:22][CH:26]=[CH:25][CH:24]=2)=[O:14])=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1Participants
Conditions
- Temperature
- 0 °C
Procedure
A solution of 2.1 g (10.0 mmol) 2-chloroquinoline-3-carboxylic acid in thionyl chloride (60 ml) was heated for 2 h at 85° C. Then excess thionyl chloride was removed under vacuum. The residue was taken up with DCM (60 ml) and the solution was cooled to 0° C. and then mixed with 4.0 ml (30.0 mmol) NEt3 and 1.03 ml (10.0 mmol) thiophene-2-methylamine. After stirring for 90 min at RT it was diluted with EE and washed with a saturated aqueous NH4Cl solution. The aqueous phase was extracted with EE. The combined organic phases were washed with brine, dried over Na2SO4, filtered and concentrated to small volume under vacuum. Column chromatography (hexane/EE 4:1) with the residue yielded 1.44 g (4.8 mmol, 48%) 2-chloro-N-(thiophen-2-ylmethyl)quinoline-3-carboxamide.
Workup
- customThen excess thionyl chloride was removed under vacuum
- additionwas diluted with EE
- washwashed with a saturated aqueous NH4Cl solution
- extractionThe aqueous phase was extracted with EE
- washThe combined organic phases were washed with brine
- dry with materialdried over Na2SO4
- filtrationfiltered
- concentrationconcentrated to small volume under vacuum
Sources & evidence
- ORD record
- ord-86a2f937289f468ba8a929400e90d358
- Source dataset
- uspto-grants-2013_03
- Patent number
- US08399673B2
Linked notes
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