Formaldehyde → Methyl 2-[3-chloro-6-(methoxy)-1,5-naphthyridin-4-yl]-2-propenoate

HRID 15302

反応式

HRID 15302 の反応式
[CH3:1][O:2][C:3](=[O:18])[CH2:4][C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([O:15][CH3:16])[N:13]=2)[N:8]=[CH:7][C:6]=1[Cl:17].[C:19](=O)([O-])[O-].[K+].[K+].C=O.C(OCC)(=O)C>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.C1CCCCC1.O>[Cl:17][C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:5]=1[C:4](=[CH2:19])[C:3]([O:2][CH3:1])=[O:18])=[N:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=2

参加物

8

反応物 4

HCID 712FormaldehydeHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 57707490Methyl [3-chloro-6-(methyloxy)-[1,5]naphthyridin-4-yl]acetate

生成物 1

HCID 57486868Methyl 2-[3-chloro-6-(methoxy)-1,5-naphthyridin-4-yl]-2-propenoate収率 89%

試薬・触媒・溶媒 3

HCID 66133Benzyl triethylammonium chloride触媒HCID 962Water溶媒HCID 8078Cyclohexane溶媒

反応条件

温度
80 °C

実験手順

A mixture of methyl[3-chloro-6-(methyloxy)-1,5-naphthyridin-4-yl]acetate (43.3 g, 162 mmol), benzyltriethylammonium chloride (71.2 g, 313 mmol), potassium carbonate (42 g, 304 mmol) and paraformaldehyde (42 g) in cyclohexane (1060 ml) was heated at 80° C. for 24 h, cooled and treated with ethyl acetate and water. After separation, the aqueous was extracted with ethyl acetate. The combined organic phases were dried and the solvent was removed. The residue was subjected to column chromatography on silica gel using hexane/15% ethyl acetate to provide the desired compound (40.2 g, 89%).

後処理

  1. temperaturecooled
  2. customAfter separation
  3. extractionthe aqueous was extracted with ethyl acetate
  4. customThe combined organic phases were dried
  5. customthe solvent was removed

出典と根拠

ORDレコード
ord-8a5f8952a0f6427990cce09d7e945dcd
出典データセット
uspto-grants-2010_06
特許番号
US07732461B2

関連ノート

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