1,2-Dichloroethane → N-methyl-3-nitropyridine-2-carboxamide

HRID 1887693

Reaction equation

HRID 1887693 reaction equation
[N+:1]([C:4]1[C:5]([C:10]([OH:12])=O)=[N:6][CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].Cl.CN.C(Cl)CCl.C1C=CC2N(O)N=[N:26][C:24]=2C=1.CCN(C(C)C)C(C)C>CN(C=O)C>[CH3:24][NH:26][C:10](=[O:12])[C:5]1[C:4]([N+:1]([O-:3])=[O:2])=[CH:9][CH:8]=[CH:7][N:6]=1

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 6364545Methylamine hydrochlorideHCID 183766123-Nitropyridine-2-carboxylic acid

Product 1

HCID 21405325N-methyl-3-nitropyridine-2-carboxamideYield 32%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 3-nitropicolinic acid (8.7 g, 51.8 mmol, 1.0 eq), methylamine hydrogen chloride (4.2 g, 1.2 eq), EDC (14.9 g, 1.5 eq), HOBt (8.4 g, 1.2 eq) in DMF (30 mL) was added DIEA (54 mL, 6.0 eq). The mixture was stirred at room temperature overnight. The crude was concentrated and dissolved in EtOAc. It was washed with saturated NaHCO3 solution. The solvent was removed and the crude was purified by silica gel chromatography (20%˜80% EtOAc/Hex) to obtain the desired product N-methyl-3-nitropicolinamide (3.0 g, isolated yield 32%).

Workup

  1. concentrationThe crude was concentrated
  2. dissolutiondissolved in EtOAc
  3. washIt was washed with saturated NaHCO3 solution
  4. customThe solvent was removed
  5. customthe crude was purified by silica gel chromatography (20%˜80% EtOAc/Hex)

Sources & evidence

ORD record
ord-bd1c65ec52a241f4a9daa8fbc4cc2667
Source dataset
uspto-grants-2013_08
Patent number
US08501763B2

Linked notes

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