1,2-Dichloroethane → 3-Amino-N,N-dimethyl-2-pyridinecarboxamide

HRID 1887697Notes

Reaction equation

HRID 1887697 reaction equation
[NH2:1][C:2]1[C:3]([C:8]([OH:10])=O)=[N:4][CH:5]=[CH:6][CH:7]=1.Cl.[CH3:12][NH:13][CH3:14].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C>CN(C=O)C>[NH2:1][C:2]1[C:3]([C:8]([N:13]([CH3:14])[CH3:12])=[O:10])=[N:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 10473Dimethylamine, hydrochlorideHCID 738363-Aminopicolinic acidHCID 757711-HydroxybenzotriazoleHCID 81531Diisopropylethylamine

Product 1

HCID 581551243-Amino-N,N-dimethyl-2-pyridinecarboxamideYield 98%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To the mixture of 3-aminopicolinic acid (0.32 g, 2.32 mmol), dimethylamine hydrogen chloride (0.227 g, 1.2 eq), EDC (0.667 g, 1.5 eq), HOBt (0.376 g, 1.2 eq) in DMF (10 mL) was added DIEA (2.0 mL, 5.0 eq). The mixture was stirred at room temperature overnight. The crude was concentrated and dissolved in EtOAc. It was washed with saturated NaHCO3. The solvent was removed and the crude was purified by silica gel chromatography (0%˜20% MeOH/DCM) to obtain the desired product 3-amino-N,N-dimethylpicolinamide (0.375 g, isolated yield ˜98%).

Workup

  1. concentrationThe crude was concentrated
  2. dissolutiondissolved in EtOAc
  3. washIt was washed with saturated NaHCO3
  4. customThe solvent was removed
  5. customthe crude was purified by silica gel chromatography (0%˜20% MeOH/DCM)

Sources & evidence

ORD record
ord-7a9eed00e3ba4e2e8605557dab917be5
Source dataset
uspto-grants-2013_08
Patent number
US08501763B2

Reaction notes

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