Methyl iodide → 1-Methyl-1H-indole-5-carboxylic acid

HRID 20979

反応式

HRID 20979 の反応式
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]([OH:12])=[O:11])=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[H-].[Na+].[CH3:15]I.[OH-].[K+]>CN(C=O)C.O>[CH3:15][N:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]([OH:12])=[O:11])=[CH:7][CH:8]=2)[CH:3]=[CH:2]1

参加物

7

反応物 4

HCID 6328Methyl iodideHCID 14797Potassium HydroxideHCID 24758Sodium hydrideHCID 742801H-Indole-5-Carboxylic Acid

生成物 1

HCID 70156011-Methyl-1H-indole-5-carboxylic acid収率 197.7%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

Indole-5-carboxylic acid (200 mg, 1.24 mmol) was dissolved in DMF (2 mL), and the solution was added with 60% sodium hydride-mineral oil dispersant (164 mg, 4.1 mmol), followed by stirring at room temperature for 10 minutes. The mixture was added with methyl iodide (0.258 mL, 0.410 mmol), stirred at room temperature for 3 hours and then added with 4 mol/L aqueous potassium hydroxide solution (2 mL), followed by stirring at 80° C. for 5 hours. The reaction mixture was added with water, and the organic layer was separated from aqueous layer. The aqueous layer was added with 1 mol/L hydrochloric acid to adjust the pH to 1, followed by stirring at room temperature for 1 hour. The obtained solid was collected by filtration and dried under reduced pressure to obtain 1-methylindole-5-carboxylic acid (142 mg, yield 65%).

後処理

  1. stirringstirred at room temperature for 3 hours
  2. stirringby stirring at 80° C. for 5 hours
  3. customthe organic layer was separated from aqueous layer
  4. additionThe aqueous layer was added with 1 mol/L hydrochloric acid
  5. stirringby stirring at room temperature for 1 hour
  6. filtrationThe obtained solid was collected by filtration
  7. customdried under reduced pressure

出典と根拠

ORDレコード
ord-77f1f3f9088640cd88e8fcb31e40bef3
出典データセット
uspto-grants-2010_06
特許番号
US07745641B2

関連ノート

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