Hexane → 6-Bromo-4-hydroxy-3-phenylquinolin-2(1H)-one

HRID 627465Notes

Reaction equation

HRID 627465 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

5

Reactant 3

HCID 8058HexaneHCID 2733832Lithium HexamethyldisilazideHCID 19168685Methyl 5-bromo-2-(2-phenylacetamido)benzoate

Product 1

HCID 867160566-Bromo-4-hydroxy-3-phenylquinolin-2(1H)-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 5-bromo-2-(2-phenylacetamido)benzoate (7.71 g, 22.1 mmol, Intermediate 1, 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 clear to clear red. The mixture was stirred at −78° C. to room temperature for 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 give the title compound. More solid was precipitated from the filtrate after standing overnight. The solid was collected by filtering, washing with water and Et2O, and air drying to afford more title compound.

Workup

  1. customThe reaction was quenched with water
  2. filtrationThe precipitated solid was filtered
  3. washwashed with water and Et2O, and air
  4. customdried

Sources & evidence

ORD record
ord-5ac3d007600b40d39829455ce2bc01e0
Source dataset
uspto-grants-2016_04
Patent number
US09309222B2

Reaction notes

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