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

HRID 1422938Notes

Reaction equation

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

Participants

Conditions

Temperature: 70 °C

Procedure

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).

Workup

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

Sources & evidence

ORD record: ord-351f8f2aa16745a0bef44f96a1d9293d
Source dataset: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08927541B2

Reaction notes

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