Dimethylformamide → HCID 86643869, compound

HRID 2382882Notes

Reaction equation

HRID 2382882 reaction equation
O[CH2:2][C:3]1[N:8]=[CH:7]C(C([O-])=O)=[CH:5][CH:4]=1.[K+].CN(C=O)C.[C:18](Cl)(=O)[C:19]([Cl:21])=[O:20].C(Cl)[Cl:25]>>[ClH:21].[Cl:25][CH2:2][C:3]1[N:8]=[CH:7][C:18]([C:19]([Cl:21])=[O:20])=[CH:5][CH:4]=1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 6344DichloromethaneHCID 65578Oxalyl chlorideHCID 23665912HCID 23665912, compound

Product 1

HCID 86643869HCID 86643869, compound

Conditions

Temperature
0 °C

Procedure

To a suspension of potassium 6-(hydroxymethyl)pyridine-3-carboxylate (96 mg; 0.50 mmol; 1.0 eq.) in DCM (1 mL) was added DMF (0.07 mg; 0.02 eq., 0.01 mmol). The mixture was chilled at 0° C. Then oxalyl chloride (317 mg; 2.5 mmol; 5.0 eq.) was added dropwise and the resulting mixture was stirred 4 h at rt. Evaporation of the solvent gave a black line powder without further purification in the next step.

Workup

  1. customEvaporation of the solvent
  2. customgave a black line powder
  3. customwithout further purification in the next step

Sources & evidence

ORD record
ord-8f0400f99d3e47038885fc23e07be298
Source dataset
uspto-grants-2012_09
Patent number
US08263595B2

Reaction notes

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