Water → 5-Chloro-1-methylindole

HRID 1017583

反応式

HRID 1017583 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[CH:5]2.[OH-].[K+].I[CH3:14].O>CN(C=O)C>[CH3:14][N:7]1[C:8]2[C:4](=[CH:3][C:2]([Cl:1])=[CH:10][CH:9]=2)[CH:5]=[CH:6]1

参加物

6

反応物 4

HCID 962WaterHCID 6328Methyl iodideHCID 14797Potassium HydroxideHCID 871105-Chloroindole

生成物 1

HCID 108558435-Chloro-1-methylindole

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
0 °C

実験手順

To room temperature solution of 5-chloroindole (4.97 g) in dry DMF (40 mL) was added potassium hydroxide pellets (2.76 g) and stirred 1 h until most of the solid dissolved. The resulting mixture was cooled to 0° C. in an ice bath and iodomethane (2.45 mL) was added dropwise and later stirred overnight at room temperature under argon. The reaction mixture was poured into water and extracted twice with ETOAc. The combined ETOAc portions were combined, washed with water, dried over magnesium sulfate, concentrated, and flash chromatographed with 10% ETOAc/Hexane to give 1-methyl-5-chloroindole as a pink liquid (5.43 g).

後処理

  1. dissolutiondissolved
  2. extractionextracted twice with ETOAc
  3. washwashed with water
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated
  6. customflash chromatographed with 10% ETOAc/Hexane

出典と根拠

ORDレコード
ord-f764d5d4ae964da5a8d063545527fe57
出典データセット
uspto-grants-2002_11
特許番号
US06479490B2

関連ノート

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