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

HRID 526826Notes

Reaction equation

HRID 526826 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 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-1ef2238fd6f54ed9adcc8e57d354451d
Source dataset
uspto-grants-2016_05
Patent number
US09346782B2

Reaction notes

Loading…