Water → 3-Chloro-1,8-naphthyridine-4-carbaldehyde

HRID 2374160노트

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HRID 2374160 반응식
[Cl:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([C:11]=1[CH3:12])=[CH:9][CH:8]=[CH:7][N:6]=2.O.[Se](=O)=[O:15].C([O-])(O)=O.[Na+]>O1CCOCC1.C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([C:11]=1[CH:12]=[O:15])=[CH:9][CH:8]=[CH:7][N:6]=2

참가 물질

7

반응물 4

HCID 962Water2회HCID 24007Selenium DioxideHCID 516892Sodium BicarbonateHCID 445975003-Chloro-4-methyl-1,8-naphthyridine

생성물 1

HCID 445966683-Chloro-1,8-naphthyridine-4-carbaldehyde수율 31.1%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 312751,4-Dioxane용매

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온도
110 °C

실험 절차

3-Chloro4-methyl-[1,8]naphthyridine (3.0 g, 16.7 mmol) from Step 3 was dissolved in 4:1 dioxane:water (30 mL) and selenium dioxide (5.9 g, 50.4 mmol) was added. The reaction mixture was heated (110° C.) for 2.5 h, cooled to RT, poured into satd. aq. NaHCO3 (30 mL) and water (10 mL). The mixture was subsequently treated with DCM (80 mL) and the solids filtered off through Celite and rinsing the filter cake with DCM. After separating the aqueous and organic layers, the aqueous phase was re-extracted with DCM (4×80 mL) and the combined organics were dried (Na2SO4) and concentrated. The crude product was chromatographed by SGC (MeCN eluant) to yield the title compound 3-chloro-[1,8]naphthyridine-4-carbaldehyde (1.0 g, 5.2 mmol). Note: owing to weak UV activity, it was found more efficacious to monitor column fractions with MS rather than UV, as in Step 3. MS (ESI+) for m/z 193 (M+H)+. 1H NMR(CDCl3)δ 10.79 (s, 1H), 9.28 (dd, 1H), 9.17 (s, 1H), 9.14 (dd, 1H), 7.63(dd. 1H).

후처리

  1. temperaturecooled to RT
  2. additionpoured into satd
  3. filtrationthe solids filtered off through Celite
  4. washrinsing the filter cake with DCM
  5. customAfter separating the aqueous and organic layers
  6. extractionthe aqueous phase was re-extracted with DCM (4×80 mL)
  7. dry with materialthe combined organics were dried (Na2SO4)
  8. concentrationconcentrated
  9. customThe crude product was chromatographed by SGC (MeCN eluant)

출처 및 근거

ORD 기록
ord-cfb726062719413b812759ede9e24b29
출처 데이터셋
uspto-grants-2008_12
특허 번호
US07462600B2

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