Water → Methyl [3-chloro-6-(methyloxy)-[1,5]naphthyridin-4-yl]acetate

HRID 15123

反応式

HRID 15123 の反応式
[Cl:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([C:11]=1[CH:12](C(OC)=O)[C:13]([O:15][CH3:16])=[O:14])=[N:9][C:8]([O:21][CH3:22])=[CH:7][CH:6]=2.[Cl-].[Li+].O.C(OCC)(=O)C>CS(C)=O>[Cl:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([C:11]=1[CH2:12][C:13]([O:15][CH3:16])=[O:14])=[N:9][C:8]([O:21][CH3:22])=[CH:7][CH:6]=2

参加物

6

反応物 4

HCID 962Water2 回HCID 8857Ethyl AcetateHCID 433294Lithium ChlorideHCID 57707472Dimethyl [3-chloro-6-(methyloxy)-1,5-naphthyridin-4-yl]propanedioate

生成物 1

HCID 57707490Methyl [3-chloro-6-(methyloxy)-[1,5]naphthyridin-4-yl]acetate収率 94%

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

反応条件

温度
100 °C

実験手順

To a solution of dimethyl [3-chloro-6-(methyloxy)-1,5-naphthyridin-4-yl]propanedioate (56 g, 173 mmol) in dimethylsulfoxide (1210 ml) was added lithium chloride (14.9 g, 350 mmol) and water (3.2 ml, 180 mmol). The mixture was heated to 100° C. for 16 hours then cooled and treated with ethyl acetate and water. The organic phase was washed twice with water, the aqueous extracted with ethyl acetate and this water-washed. The combined organic phases were dried and the solvent was removed under reduced pressure. The residue was subjected to column chromatography on silica gel using a hexane and ethyl acetate gradient to provide the desired compound (43 g, 94%).

後処理

  1. temperaturethen cooled
  2. washThe organic phase was washed twice with water
  3. extractionthe aqueous extracted with ethyl acetate
  4. washthis water-washed
  5. customThe combined organic phases were dried
  6. customthe solvent was removed under reduced pressure

出典と根拠

ORDレコード
ord-a1419524ecf446e093454396f5698dbf
出典データセット
uspto-grants-2010_06
特許番号
US07732460B2

関連ノート

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