Picolinic acid → 4-chloro-N-(2-(dimethylamino)ethyl)picolinamide

HRID 1994107Notes

Reaction equation

HRID 1994107 reaction equation
S(Cl)([Cl:3])=O.[N:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11]([OH:13])=O.[CH3:14][N:15]([CH3:19])[CH2:16][CH2:17][NH2:18]>CN(C=O)C>[Cl:3][C:8]1[CH:9]=[CH:10][N:5]=[C:6]([C:11]([NH:18][CH2:17][CH2:16][N:15]([CH3:19])[CH3:14])=[O:13])[CH:7]=1

Participants

5

Reactant 3

HCID 1018Picolinic acidHCID 24386Thionyl ChlorideHCID 66053N,N-Dimethylethylenediamine

Product 1

HCID 430882584-chloro-N-(2-(dimethylamino)ethyl)picolinamideYield 46%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
95 °C

Procedure

To a solution of thionyl chloride (7.4 mL, 101 mmol) in DMF was added pyridine-2-carboxylic acid (2.5 g, 20.3 mmol). The reaction mixture was heated at 95° C. for 12 h and then concentrated. The residue was redissolved in DMF (7 mL) and N,N-dimethylethane-1,2-diamine (11 mL, 101.5 mmol) was added. After stirring for 15 min, the mixture was concentrated and the residue was purified by column chromatography (0-10% methanol/dichloromethane) to yield 2.11 g of the title compound (46%). LCMS: (FA) ES+ 227.9 (M+1)

Workup

  1. concentrationconcentrated
  2. dissolutionThe residue was redissolved in DMF (7 mL)
  3. concentrationthe mixture was concentrated
  4. customthe residue was purified by column chromatography (0-10% methanol/dichloromethane)

Sources & evidence

ORD record
ord-e8b0e4b2ba9b43ae8e9d601173cb4460
Source dataset
uspto-grants-2010_01
Patent number
US07652041B2

Reaction notes

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