3-Pyridineacetic acid → 2-(Pyridin-3-yl)acetyl chloride

HRID 2382897Notes

Reaction equation

HRID 2382897 reaction equation
[C:1](Cl)(=O)[C:2]([Cl:4])=[O:3].[N:7]1[CH:12]=[CH:11][CH:10]=[C:9](CC(O)=O)[CH:8]=1>C(Cl)Cl.CN(C=O)C>[N:7]1[CH:12]=[CH:11][CH:10]=[C:9]([CH2:1][C:2]([Cl:4])=[O:3])[CH:8]=1

Participants

4

Reactant 2

HCID 1083-Pyridineacetic acidHCID 65578Oxalyl chloride

Product 1

HCID 146974752-(Pyridin-3-yl)acetyl chloride

Reagents, catalysts & solvents 1

HCID 22350042dichloromethane N,N-dimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

Oxalyl chloride (211 μl; 2.23 mmol; 1.2 eq.) was added to a suspension of 3-pyridineacetic acid (255 mg; 1.86 mmol; 1.0 eq.) in DCM/DMF (5 mL:3 μL) maintained at 0° C. under nitrogen atmosphere. The reaction mixture was then stirred at rt for 1 h. It was then concentrated under reduced pressure. The solid obtained was used as such in amidation reactions.

Workup

  1. concentrationIt was then concentrated under reduced pressure
  2. customThe solid obtained

Sources & evidence

ORD record
ord-7bbd1025857f4cfb919bb62b3a1b06f1
Source dataset
uspto-grants-2012_09
Patent number
US08263595B2

Reaction notes

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