Hydrogen Peroxide → 3-Benzyloxy-6-methoxy-[1,5]naphthyridine-4-carboxylic acid amide

HRID 1422938노트

반응식

HRID 1422938 반응식
OO.[CH2:3]([O:10][C:11]1[CH:12]=[N:13][C:14]2[C:19]([C:20]=1[C:21]#[N:22])=[N:18][C:17]([O:23][CH3:24])=[CH:16][CH:15]=2)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[OH-].[Na+].C(OCC)(=[O:29])C>CO.[O-2].[O-2].[Mn+4]>[CH2:3]([O:10][C:11]1[CH:12]=[N:13][C:14]2[C:19]([C:20]=1[C:21]([NH2:22])=[O:29])=[N:18][C:17]([O:23][CH3:24])=[CH:16][CH:15]=2)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

참가 물질

7

반응물 4

HCID 784Hydrogen PeroxideHCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 672570043-Benzyloxy-6-methoxy-[1,5]naphthyridine-4-carbonitrile

생성물 1

HCID 672539813-Benzyloxy-6-methoxy-[1,5]naphthyridine-4-carboxylic acid amide수율 75%

시약·촉매·용매 2

HCID 178418406HCID 178418406, 화합물촉매HCID 887Methanol용매

반응 조건

온도
70 °C

실험 절차

30% Hydrogen peroxide (17.2 mmol, 5.0 eq) is added dropwise at room temperature to a stirred suspension of 3-benzyloxy-6-methoxy-[1,5]naphthyridine-4-carbonitrile (1.0 g, 3.43 mmol, 1.0 eq) and sodium hydroxide (69 mg, 0.17 mmol, 0.05 eq) in methanol (100 mL). After 1 hour stirring at 70° C., a catalytic amount of manganese dioxide is added to the reaction mixture that is concentrated to give a crude that is purified by column chromatography (silica gel, eluent: petroleum ether:ethyl acetate, 1:1, v/v) to afford 3-benzyloxy-6-methoxy-[1,5]naphthyridine-4-carboxylic acid amide as a white solid (800 mg, 75% yield).

후처리

  1. concentrationis concentrated
  2. customto give a crude that
  3. customis purified by column chromatography (silica gel, eluent

출처 및 근거

ORD 기록
ord-351f8f2aa16745a0bef44f96a1d9293d
출처 데이터셋
uspto-grants-2015_01
특허 번호
US08927541B2

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