Dimethylformamide → 2-Chloro-3-chloromethyl-pyridine

HRID 626352Notes

Reaction equation

HRID 626352 reaction equation
[Cl:1][C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4](O)=O.C(Cl)(=O)C([Cl:14])=O.CN(C)C=O>C(Cl)Cl>[Cl:1][C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[CH2:4][Cl:14]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 762582-Chloronicotinic acid

Product 1

HCID 115283992-Chloro-3-chloromethyl-pyridine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To the solution of 2-choronicotinic acid (5 g, 31.84 mmol) in dry DCM under nitrogen, Oxalyl chloride (38.21 mmol) and catalytic amount of N,N-dimethylformamide were added carefully with stirring. The reaction was stirred for 3 hr. The solution was concentrated under vacuum to yield 2-chloronicotinyl chloride as solid which was used for next reaction without purification.

Workup

  1. stirringThe reaction was stirred for 3 hr
  2. concentrationThe solution was concentrated under vacuum

Sources & evidence

ORD record
ord-826011faec864bcdad8df2542854a982
Source dataset
uspto-grants-2016_04
Patent number
US09309225B2

Reaction notes

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