Hydrochloric Acid → HCID 178515444, compound
Reaction equation
[Br:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]([C:19]3[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=3)([C:14]3[S:15][CH:16]=[CH:17][N:18]=3)O)[CH:10]=2)[N:5]=[C:4]([O:26]C(C)(C)C)[CH:3]=1.Cl.Cl[Sn]Cl.O>CC(O)=O>[Br:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([CH:12]([C:19]3[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=3)[C:14]3[S:15][CH:16]=[CH:17][N:18]=3)[CH:10]=2)[N:5]=[C:4]([OH:26])[CH:3]=1Participants
Conditions
- Temperature
- 100 °C
Procedure
Into a 250-mL round-bottom flask, was placed [4-bromo-2-(tert-butoxy)quinolin-6-yl](4-chlorophenyl)1,3-thiazol-2-ylmethanol (5.5 g, 10.92 mmol, 1.00 equip), AcOH (78 mL), hydrogen chloride (13 mL), and SnCl2.2 H2O (7.4 g, 32.80 mmol, 3.00 equip). The resulting solution was stirred for 40 min at 100° C. The resulting mixture was concentrated under vacuum. The resulting solution was diluted with water (200 mL). The resulting solution was extracted with DCM (3×200 mL) and the organic layers combined. The resulting mixture was washed with water (2×200 mL). The resulting mixture was dried over anhydrous sodium sulfate. The residue was applied onto a silica gel column with dichloromethane:methanol (10:1) to yield 4-bromo-6-[(4-chlorophenyl)(1,3-thiazol-2-yl)methyl]quinolin-2-ol as a white solid. (ES, m/z): [M+N]+ 433
Workup
- customInto a 250-mL round-bottom flask, was placed
- concentrationThe resulting mixture was concentrated under vacuum
- additionThe resulting solution was diluted with water (200 mL)
- extractionThe resulting solution was extracted with DCM (3×200 mL)
- washThe resulting mixture was washed with water (2×200 mL)
- dry with materialThe resulting mixture was dried over anhydrous sodium sulfate
Sources & evidence
- ORD record
- ord-b17924c993b14edf9b87c2ec6b8b3b96
- Source dataset
- uspto-grants-2016_02
- Patent number
- US09266835B2
Reaction notes
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