N,O-Dimethylhydroxylamine → N-Methoxy-N-methylquinoline-6-carboxamide

HRID 16022

반응식

HRID 16022 반응식
[N:1]1[C:10]2[C:5](=[CH:6][C:7]([C:11]([OH:13])=O)=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.C(C1NC=CN=1)(C1NC=CN=1)=O.[CH3:26][NH:27][O:28][CH3:29]>CN(C=O)C.CCOC(C)=O.O>[CH3:29][O:28][N:27]([CH3:26])[C:11]([C:7]1[CH:6]=[C:5]2[C:10](=[CH:9][CH:8]=1)[N:1]=[CH:2][CH:3]=[CH:4]2)=[O:13]

참가 물질

7

반응물 3

HCID 14232N,O-DimethylhydroxylamineHCID 825716-Quinolinecarboxylic acidHCID 5250894Bis-(1H-imidazol-2-YL)-methanone

생성물 1

HCID 55211172N-Methoxy-N-methylquinoline-6-carboxamide수율 97%

시약·촉매·용매 3

HCID 962Water용매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of quinoline-6-carboxylic acid (10 g, 57.75 mmol) in DMF (200 mL) was added carbonyl diimidazole (10.3 g, 62.5 mmol) under nitrogen. The reaction was stirred for 1 hour. To the solution was added N,O-dimethyl hydroxylamine (5.6 g, 57.75 mmol), and the reaction was stirred at ambient temperature for 16 hours. The reaction was diluted with EtOAc (150 mL) and water (150 mL). The organic layer was separated, and the aqueous layer was extracted with EtOAc (5×100 mL). The organics were combined and washed with water (3×100 mL), brine (2×100 mL), dried over Na2SO4, filtered and concentrated to give quinoline-6-carboxylic acid methoxy-methyl-amide (11.97 g, 97% yield).

후처리

  1. stirringthe reaction was stirred at ambient temperature for 16 hours
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was extracted with EtOAc (5×100 mL)
  4. washwashed with water (3×100 mL), brine (2×100 mL)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

출처 및 근거

ORD 기록
ord-62bc40f4074643f5a8f11e7706291891
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07732604B2

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