Methyl iodide → 1-Methyl-1H-indole-6-carboxylic acid

HRID 20980

반응식

HRID 20980 반응식
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:10]([OH:12])=[O:11])[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][CH:6]=[C:7]([C:10]([OH:12])=[O:11])[CH:8]=2)[CH:3]=[CH:2]1

참가 물질

7

반응물 4

HCID 6328Methyl iodideHCID 14797Potassium HydroxideHCID 24758Sodium hydrideHCID 5952301H-indole-6-carboxylic acid

생성물 1

HCID 198192611-Methyl-1H-indole-6-carboxylic acid수율 214.4%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

In a similar manner to Step 1 of Reference Example 12, indole-6-carboxylic acid (200 mg, 1.24 mmol) was dissolved in DMF (2 mL), and the solution was treated with 60% sodium hydride-mineral oil dispersant (109 mg, 2.71 mmol), methyl iodide (0.258 mL, 0.410 mmol) and 4 mol/L aqueous potassium hydroxide solution (2 mL). The reaction mixture was added with water and separated into aqueous layer and organic layer, and the organic layer was removed. 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-6-carboxylic acid (154 mg, yield 71%).

후처리

  1. customseparated into aqueous layer and organic layer
  2. customthe organic layer was removed
  3. additionThe aqueous layer was added with 1 mol/L hydrochloric acid
  4. filtrationThe obtained solid was collected by filtration
  5. customdried under reduced pressure

출처 및 근거

ORD 기록
ord-a5aefe6165594ef5bfe0f2092a468033
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07745641B2

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