Acetyl chloride → quinolin-6-yl acetate

HRID 1890932Notes

Reaction equation

HRID 1890932 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][C:7]([OH:11])=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[C:12](Cl)(=[O:14])[CH3:13]>N1C=CC=CC=1>[N:1]1[C:10]2[C:5](=[CH:6][C:7]([O:11][C:12](=[O:14])[CH3:13])=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 113746-Hydroxyquinoline

Product 1

HCID 459602quinolin-6-yl acetateYield 69%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
0 °C

Procedure

Quinolin-6-ol (135 g, 0.93 mol) was dissolved in pyridine (500 mL) and cooled to 0° C. in an ice-bath under a flow of nitrogen. Acetyl chloride (79 mL, 1.16 mol) was added to the reaction mixture slowly. Then it was stirred at room temperature for 3 hours. The mixture was partitioned between ethyl acetate (400 mL) and saturated aqueous NaHCO3 (200 mL). The organic phase was separated and washed with brine (5*200 mL). The organic phase was dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by column chromatography to afford 120 g of acetic acid quinolin-6-yl ester as white solid (69% yield).

Workup

  1. customThe mixture was partitioned between ethyl acetate (400 mL) and saturated aqueous NaHCO3 (200 mL)
  2. customThe organic phase was separated
  3. washwashed with brine (5*200 mL)
  4. dry with materialThe organic phase was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-2f03704c961f4797a296c4dd725e0fa8
Source dataset
uspto-grants-2013_08
Patent number
US08507489B2

Reaction notes

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