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

HRID 2273261
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HRID 2273261 반응식
[Cl:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([C:11]=1[C:12](N)=[O:13])=[N:9][C:8]([O:15][CH3:16])=[CH:7][CH:6]=2>O1CCCC1.Cl.C1([Zr]C2C=CC=C2)C=CC=C1>[Cl:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([C:11]=1[CH:12]=[O:13])=[N:9][C:8]([O:15][CH3:16])=[CH:7][CH:6]=2
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참가 물질

4

반응물 1

HCID 672571323-Chloro-6-methoxy-[1,5]naphthyridine-4-carboxylic acid amide

생성물 1

HCID 866715503-Chloro-6-methoxy-[1,5]naphthyridine-4-carbaldehyde수율 39.6%

시약·촉매·용매 2

HCID 178420596HCID 178420596, 화합물촉매HCID 8028Tetrahydrofuran용매

실험 절차

Bis(cyclopentadienyl)zirconium hydrochloride (814 mg, 3.2 mmol, 1.5 eq) is added at room temperature to a stirred solution of 3-chloro-6-methoxy-[1,5]naphthyridine-4-carboxylic acid amide (500 mg, 2.1 mmol, 1.0 eq) in tetrahydrofuran (35 mL). After 10 minutes stirring at room temperature, the reaction mixture is filtered through decalite, concentrated and purified by column chromatography (silica gel, eluent: ethyl acetate:petroleum ether, 1:8, v/v) to afford 3-chloro-6-methoxy-[1,5]naphthyridine-4-carbaldehyde as an off-white solid (185 mg, 28% yield).

후처리

  1. filtrationthe reaction mixture is filtered through decalite,
  2. concentrationconcentrated
  3. custompurified by column chromatography (silica gel, eluent: ethyl acetate:petroleum ether, 1:8, v/v)

출처 및 근거

ORD 기록
ord-0ca58ee815d64982bbabecf010acd922
출처 데이터셋
uspto-grants-2015_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09120822B2

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