Methylamine → Ethyl 4-hydroxy-1,2,5-trimethyl-6-oxo-1,6-dihydropyridine-3-carboxylate

HRID 422779

反応式

HRID 422779 の反応式
C(O[C:4](=[O:15])[CH:5]([CH3:14])[C:6](=[O:13])[CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])C.C(OC(O[CH2:22][CH3:23])=C)C.[CH3:24][NH2:25]>C(OCC)C.C[O-].[Na+]>[CH2:11]([O:10][C:8]([C:7]1[C:6]([OH:13])=[C:5]([CH3:14])[C:4](=[O:15])[N:25]([CH3:24])[C:22]=1[CH3:23])=[O:9])[CH3:12]

参加物

6

反応物 3

HCID 6329MethylamineHCID 1376731,1-DiethoxyetheneHCID 10921903Diethyl 2-methyl-3-oxopentanedioate

生成物 1

HCID 66673467Ethyl 4-hydroxy-1,2,5-trimethyl-6-oxo-1,6-dihydropyridine-3-carboxylate収率 34%

試薬・触媒・溶媒 2

HCID 10942334Sodium Methoxide触媒HCID 3283Diethyl Ether溶媒

反応条件

温度
85 °C

実験手順

A mixture of 2-methyl-3-oxo-pentanedioic acid diethyl ester (10.0 g, 46.3 mmol), 1,1-diethoxy-ethene (12.8 mL, 92.5 mmol) and sodium methoxide (0.026 mg, 0.481 mmol) was heated to 85° C. for nine hours. The reaction mixture was cooled to room temperature and concentrated. To the resulting residue was added methylamine (1.91 mL, 55.5 mmol, 40% H2O). After stirring at room temperature for 16 hours, the reaction mixture was diluted with diethyl ether and washed with water. The aqueous phase was acidified to pH 1 with 10% HCl solution and extracted with EtOAc. The organic layer was dried (MgSO4) and concentrated. Trituration of the resulting residue with diethyl ether and flash column chromatography (3% MeOH in methylene chloride) gave 3.55 g (34%) desired product.

後処理

  1. temperatureThe reaction mixture was cooled to room temperature
  2. concentrationconcentrated
  3. washwashed with water
  4. extractionextracted with EtOAc
  5. dry with materialThe organic layer was dried (MgSO4)
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-641f7e13a9f343208d3e6d132e3d7ff0
出典データセット
uspto-grants-2012_01
特許番号
US08101639B2

関連ノート

読み込み中…