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

HRID 2374160ノート

反応式

HRID 2374160 の反応式
[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

参加物

7

反応物 4

HCID 962Water2 回HCID 24007Selenium DioxideHCID 516892Sodium BicarbonateHCID 445975003-Chloro-4-methyl-1,8-naphthyridine

生成物 1

HCID 445966683-Chloro-1,8-naphthyridine-4-carbaldehyde収率 31.1%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
110 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-cfb726062719413b812759ede9e24b29
出典データセット
uspto-grants-2008_12
特許番号
US07462600B2

反応ノート

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