Acetyl chloride → Methyl (6-chloropyridin-3-yl)acetate

HRID 576657Notes

Reaction equation

HRID 576657 reaction equation
[C:1](Cl)(=O)C.[Cl:5][C:6]1[N:11]=[CH:10][C:9]([CH2:12][C:13]([OH:15])=[O:14])=[CH:8][CH:7]=1>CO>[Cl:5][C:6]1[N:11]=[CH:10][C:9]([CH2:12][C:13]([O:15][CH3:1])=[O:14])=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 140715712-(6-Chloropyridin-3-yl)acetic acid

Product 1

HCID 53419528Methyl (6-chloropyridin-3-yl)acetate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of MeOH (25 mL) was added slowly acetyl chloride (3.5 mL). After 30 min, 2-(6-chloropyridin-3-yl)acetic acid (2.5 g) was added and the resulting reaction mixture stirred at room temperature for 2 hr. Solvents were then removed. The residue was dissolved in EtOAc and washed with 10% NaHCO3. The organic phase was dried and concentrated to afford the product (2.5 g).

Workup

  1. customthe resulting reaction mixture
  2. customSolvents were then removed
  3. dissolutionThe residue was dissolved in EtOAc
  4. washwashed with 10% NaHCO3
  5. customThe organic phase was dried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-94b96c9fade74805bc5e949afb46d2c8
Source dataset
uspto-grants-2015_05
Patent number
US09040504B2

Reaction notes

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