Sodium Hydroxide → 3-Chloro-6-methoxy-[1,5]naphthyridine-4-carboxylic acid amide

HRID 2273260노트

반응식

HRID 2273260 반응식
[Cl:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([C:11]=1[C:12]#[N:13])=[N:9][C:8]([O:14][CH3:15])=[CH:7][CH:6]=2.[OH-:16].[Na+]>C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([C:11]=1[C:12]([NH2:13])=[O:16])=[N:9][C:8]([O:14][CH3:15])=[CH:7][CH:6]=2

참가 물질

4

반응물 2

HCID 14798Sodium HydroxideHCID 672545843-Chloro-6-methoxy-[1,5]naphthyridine-4-carbonitrile

생성물 1

HCID 672571323-Chloro-6-methoxy-[1,5]naphthyridine-4-carboxylic acid amide수율 64%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

3-Chloro-6-methoxy-[1,5]naphthyridine-4-carbonitrile (5.0 g, 22.8 mmol, 1.0 eq) is suspended in a 10% sodium hydroxide aqueous solution (125 mL) and the resulting mixture is heated to reflux for 30 minutes. The reaction mixture is then extracted with ethyl acetate (3×100 mL) and the pH is adjusted to 3-4 by the addition of a 3N hydrochloric acid aqueous solution. The combined organic layers are dried over sodium sulfate, filtered and concentrated to give the crude product that is purified by column chromatography (silica gel, eluent: ethyl acetate:petroleum ether, 1:1 to 4:1, v/v) to afford 3-chloro-6-methoxy-[1,5]naphthyridine-4-carboxylic acid amide as an off-white solid (3.44 g, 64% yield).

후처리

  1. temperaturethe resulting mixture is heated
  2. temperatureto reflux for 30 minutes
  3. extractionThe reaction mixture is then extracted with ethyl acetate (3×100 mL)
  4. additionthe pH is adjusted to 3-4 by the addition of a 3N hydrochloric acid aqueous solution
  5. dry with materialThe combined organic layers are dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give the crude product that
  9. customis purified by column chromatography (silica gel, eluent

출처 및 근거

ORD 기록
ord-761c4c9fd0da4d7089852d126d3a0994
출처 데이터셋
uspto-grants-2015_09
특허 번호
US09120822B2

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