Water → 4-Methoxyindole-3-aldehyde

HRID 1371872

反応式

HRID 1371872 の反応式
P(Cl)(Cl)(Cl)=O.[CH3:6][O:7][C:8]1[CH:16]=[CH:15][CH:14]=[C:13]2[C:9]=1[CH:10]=[CH:11][NH:12]2.[OH-].[Na+].O.CN([CH:23]=[O:24])C>>[CH:23]([C:10]1[C:9]2[C:13](=[CH:14][CH:15]=[CH:16][C:8]=2[O:7][CH3:6])[NH:12][CH:11]=1)=[O:24]

参加物

6

反応物 5

HCID 962WaterHCID 6228Dimethylformamide2 回HCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 1383634-Methoxy-1H-indole

生成物 1

HCID 1462294-Methoxyindole-3-aldehyde

反応条件

温度
0 °C

実験手順

Add phosphorus oxychloride (1.1 eq.) with vigorous stirring to DMF (cooled in an ice bath). After the addition is complete, allow to stir in the ice bath for ˜10 minutes, then add a solution of 4-methoxy-1H-indole (5 g) in anhydrous DMF with vigorous stirring. Allow to stir at 0° C. After 1 hour, warm to room temperature. After 16 hours, carefully add 4 eq. of 2N NaOH with vigorous stirring. Heat to about 80° C. and then cool. Pour the reaction mixture into cold water with vigorous stirring to give a solid. Collect the solid by filtration and dry in a vacuum oven at room temperature to give the title compound. Acidify the filtrate and extract with EtOAc. Combine the organic layers and wash with 50% brine. Collect the organic layer, dry (MgSO4) filter, and remove the solvent to give the title compound as a light purple solid. Total yield of the title compound is 5.44 g: MS (ES+): m/z 175 (M+H)+, 160 (M-CH3)+; (ES−): m/z 174 (M−H)−.

後処理

  1. additionAfter the addition
  2. temperaturewarm to room temperature
  3. waitAfter 16 hours
  4. temperatureHeat to about 80° C.
  5. temperaturecool
  6. stirringwith vigorous stirring
  7. customto give a solid
  8. customCollect the solid
  9. filtrationby filtration
  10. customdry in a vacuum oven at room temperature

出典と根拠

ORDレコード
ord-ac7aa54576f34876ab88535244de0b83
出典データセット
uspto-grants-2007_01
特許番号
US07157488B2

関連ノート

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