Sodium Bicarbonate → 2-(Chloromethyl)quinoline

HRID 1752588Notes

Reaction equation

HRID 1752588 reaction equation
Cl.[Cl:2][CH2:3][C:4]1[CH:13]=[CH:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=1.C(=O)([O-])O.[Na+]>CC(=O)OCC.O>[Cl:2][CH2:3][C:4]1[CH:13]=[CH:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=1

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 30838232-(Chloromethyl)quinoline hydrochloride

Product 1

HCID 203942-(Chloromethyl)quinolineYield 96%

Reagents, catalysts & solvents 1

HCID 22728543Water ethylacetateSolvent

Procedure

To a suspension of 2-(chloromethyl)quinoline hydrochloride (10 g, 46.7 mmol) in EA/water (150 ml: 75 ml) was added sodium hydrogencarbonate powder portionwise until gas evolution ceased. The organic layer was collected, washed with brine (3×50 ml), dried over sodium sulfate and concentrated. The obtained crude title compound was used in without further purification (8 g, 96% yield).

Workup

  1. customThe organic layer was collected
  2. washwashed with brine (3×50 ml)
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-8706a577b52b4f50bdb129f17ddebcdc
Source dataset
uspto-grants-2015_10
Patent number
US09163019B2

Reaction notes

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