Hydrochloric Acid → 1-(6-Bromoquinolin-2-yl)ethanone

HRID 1471189Notes

Reaction equation

HRID 1471189 reaction equation
Cl.[Br:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[C:8]([C:13]([O:15]CC)=[CH2:14])[CH:7]=[CH:6]2>CC(C)=O>[Br:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[C:8]([C:13](=[O:15])[CH3:14])[CH:7]=[CH:6]2

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 584987316-Bromo-2-(1-ethoxyvinyl)quinoline

Product 1

HCID 574581651-(6-Bromoquinolin-2-yl)ethanoneYield 101.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

3M HCl(aq.) (10 mL, 30.0 mmol) was added to a suspension of 6-bromo-2-(1-ethoxyvinyl)quinoline (780 mg, 2.80 mmol) in acetone (20 mL) and the reaction mixture was stirred at rt for 5 h. The reaction mixture was concentrated, dissolved into THF (20 mL) and treated with 3N HCl (aq.) (5 mL) was clear reaction solution was stirred at 60° C. for 5 h. The reaction was, cooled, neutralized with aq. NaOH and NaHCO3 and extracted with EtOAc. The organic layer was dried, and concentrated to yield crude 1-(6-bromoquinolin-2-yl)ethanone (710 mg) as white solid. LC-MS retention time 3.703 min; m/z 250, 251.99 (1:1) (MH+). LC data was recorded on a Shimadzu LC-10AS liquid chromatograph equipped with a PHENOMENEX® Luna 3u C18 2.0×50 mm column using a SPD-10AV UV-Vis detector at a detector wave length of 220 nM. The elution conditions employed a flow rate of 0.8 mL/min, a gradient of 100% Solvent A/0% Solvent B to 0% Solvent A/100% Solvent B, a gradient time of 4 min, a hold time of 1 min, and an analysis time of 5 min where Solvent A was 10% MeOH/90% H2O/0.1% trifluoroacetic acid and Solvent B was 10% H2O/90% MeOH/0.1% trifluoroacetic acid. MS data was determined using a MICROMASS® Platform for LC in electrospray mode.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. dissolutiondissolved into THF (20 mL)
  3. additiontreated with 3N HCl (aq.) (5 mL)
  4. stirringwas stirred at 60° C. for 5 h
  5. temperaturecooled
  6. extractionextracted with EtOAc
  7. customThe organic layer was dried
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-aeed55a7694c465eb893f2c757f4f637
Source dataset
uspto-grants-2015_04
Patent number
US09006455B2

Reaction notes

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