1,2-Dichloroethane → 2-Amino-N-methylpyridine-3-carboxamide

HRID 1887703Notes

Reaction equation

HRID 1887703 reaction equation
[NH2:1][C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.Cl.CN.C(Cl)CCl.C1C=CC2N(O)N=[N:24][C:22]=2C=1.CCN(C(C)C)C(C)C>CN(C=O)C>[NH2:1][C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([NH:24][CH3:22])=[O:6]

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 729302-Aminonicotinic acidHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 6364545Methylamine hydrochloride

Product 1

HCID 205853262-Amino-N-methylpyridine-3-carboxamideYield 98.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To the mixture of 2-aminonicotinic acid (2.0 g, 14.5 mmol), methylamine hydrogen chloride (1.47 g, 1.5 eq), EDC (4.49 g, 1.5 eq), HOBt (2.35 g, 1.2 eq) in DMF (20 mL) was added DIEA (7.6 mL, 3.0 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 2-amino-N-methylnicotinamide (2.16 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-b6aec88fc52e4d6880e8b85dcf8f4ab0
Source dataset
uspto-grants-2013_08
Patent number
US08501763B2

Reaction notes

Loading…