4-Hydroxymethyl-6-methoxy-[1,5]naphthyridin-3-ol → 3-Hydroxy-6-methoxy-[1,5]naphthyridine-4-carbaldehyde

HRID 633794Notes

Reaction equation

[OH:1][CH2:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([O:13][CH3:14])[N:11]=2)[N:6]=[CH:5][C:4]=1[OH:15]>C(#N)C.[O-2].[O-2].[Mn+4]>[OH:15][C:4]1[CH:5]=[N:6][C:7]2[C:12]([C:3]=1[CH:2]=[O:1])=[N:11][C:10]([O:13][CH3:14])=[CH:9][CH:8]=2

Participants

Conditions

Temperature: 35 °C

Procedure

Manganese dioxide (530 mg, 6.05 mmol, 5.0 eq) is added at room temperature to a stirred solution of 4-hydroxymethyl-6-methoxy-[1,5]naphthyridin-3-ol (250 mg, 1.21 mmol, 1.0 eq) in acetonitrile (10 mL) and the resulting mixture is stirred at 35° C. for 1 hour. The solid is filtered off, washed with acetone (3×10 mL) and the filtrate is concentrated to give a residue that is purified by column chromatography (silica gel, eluent: petroleum ether:ethyl acetate, 1:4, v/v) to afford 3-hydroxy-6-methoxy-[1,5]naphthyridine-4-carbaldehyde as a light yellow solid (180 mg, 73% yield).

Workup

filtrationThe solid is filtered off
washwashed with acetone (3×10 mL)
concentrationthe filtrate is concentrated
customto give a residue that
customis purified by column chromatography (silica gel, eluent: petroleum ether:ethyl acetate, 1:4, v/v)

Sources & evidence

ORD record: ord-f6b08ee70e17412881aa80ae02bfe946
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09321788B2

Reaction notes

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