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

HRID 1507286Notes

Reaction equation

HRID 1507286 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 colorless 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 provide 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 additional 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-c31ff77c91154dbe9553830212dbb6cd
Source dataset
uspto-grants-2015_12
Patent number
US09221804B2

Reaction notes

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