Hexane → 6-Bromo-4-hydroxy-3-phenylquinolin-2(1H)-one
Reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([NH:12][C:13](=[O:21])[CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[C:6]([CH:11]=1)[C:7]([O:9]C)=O.C[Si]([N-][Si](C)(C)C)(C)C.[Li+].CCCCCC>C1COCC1>[Br:1][C:2]1[CH:11]=[C:6]2[C:5](=[CH:4][CH:3]=1)[NH:12][C:13](=[O:21])[C:14]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[C:7]2[OH:9]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
To a solution of methyl 5-bromo-2-(2-phenylacetamido)benzoate (7.71 g, 22.1 mmol, Intermediate 7: step a) in THF (50 mL) at −78° C. was added 1.0 M lithium bis(trimethylsilyl)amide in hexane (48.7 mL, 48.7 mmol) slowly, and the color changed from colorless to clear red. The mixture, at −78° C., was warmed to room temperature over 4 hours, during which time the color changed to cloudy yellow. The reaction was quenched with water, and acidified with 37% HCl until pH˜5. The precipitated solid was filtered, washed with water and Et2O, and air dried to provide the title compound. Another crop precipitated from the filtrate after standing overnight. The solid was collected by filtration, washing with water and Et2O, and air drying to afford additional title compound.
Workup
- customThe reaction was quenched with water
- filtrationThe precipitated solid was filtered
- washwashed with water and Et2O, and air
- customdried
Sources & evidence
- ORD record
- ord-b26a3f961f9844e092abdb735515f797
- Source dataset
- uspto-grants-2016_08
- Patent number
- US09403816B2
Reaction notes
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