HCID 10375029、化合物 → 3-Hydroxy-4-methyl-2-pyridinecarboxaldehyde

HRID 1198733ノート

反応式

HRID 1198733 の反応式
[O:1]1CCO[CH:2]1[C:6]1[C:11](N)=[C:10]([CH3:13])[CH:9]=[CH:8][N:7]=1.N([O-])=[O:15].[Na+]>OS(O)(=O)=O.O>[OH:15][C:11]1[C:6]([CH:2]=[O:1])=[N:7][CH:8]=[CH:9][C:10]=1[CH3:13]

参加物

5

反応物 2

HCID 10375029HCID 10375029、化合物HCID 23668193Sodium Nitrite

生成物 1

HCID 103293503-Hydroxy-4-methyl-2-pyridinecarboxaldehyde

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 1118Sulfuric Acid溶媒

反応条件

温度
0 °C

実験手順

To a solution of 2-(1,3-dioxolanyl)-4-methyl-3-aminopyridine (0.60 g, 3.3 mmol) in 15 mL of 10% H2SO4 at 0° C. (ice bath) with stirring was added dropwise a solution of NaNO2 (0.38 g, 5.5 mmol) in 3 mL of water. The mixture was stirred at 0° C. for 15 min and then heated in a steam-bath for 30 min. The resulting solution was evaporated at room temperature under reduced pressure to yield 3-hydroxy-4-methyl-2-formylpyridine as a syrup, which was dissolved in 15 mL of water, decolorized with charcoal and filtered. To the filtrate was added a solution of thiosemicarbazide (0.31 g, 3.3 mmol) in 5 mL of 5% HCl. The mixture was refluxed for 30 min, cooled and the yellow precipitate was filtered, washed with water, and recrystallized from aqueous ethanol solution (1:1, v/v) containing 5% conc. HCl to afford 0.21 g (30%) of product: the mp and all spectroscopic data were identical with those obtained in Example XLIII.

後処理

  1. temperatureheated in a steam-bath for 30 min
  2. customThe resulting solution was evaporated at room temperature under reduced pressure

出典と根拠

ORDレコード
ord-6188146fde554b90975cdc3fd202d387
出典データセット
uspto-grants-1994_01
特許番号
US05281715

反応ノート

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