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

HRID 633794노트

반응식

HRID 633794 반응식
[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

참가 물질

4

반응물 1

HCID 1363983214-Hydroxymethyl-6-methoxy-[1,5]naphthyridin-3-ol

생성물 1

HCID 1363413973-Hydroxy-6-methoxy-[1,5]naphthyridine-4-carbaldehyde수율 73%

시약·촉매·용매 2

HCID 178418406HCID 178418406, 화합물촉매HCID 6342Acetonitrile용매

반응 조건

온도
35 °C

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-f6b08ee70e17412881aa80ae02bfe946
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09321788B2

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