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

HRID 1887693

반응식

HRID 1887693 반응식
[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

참가 물질

7

반응물 5

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-bd1c65ec52a241f4a9daa8fbc4cc2667
출처 데이터셋
uspto-grants-2013_08
특허 번호
US08501763B2

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