Sodium Hydroxide → 1-(5-Methoxy-2-methyl-1H-indol-3-yl)ethanone

HRID 1461452

反応式

HRID 1461452 の反応式
P(Cl)(Cl)(Cl)=O.[CH3:6][O:7][C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[NH:13][C:12]([CH3:17])=[CH:11]2.[OH-].[Na+].[CH3:20][C:21](N(C)C)=[O:22]>O>[CH3:6][O:7][C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[NH:13][C:12]([CH3:17])=[C:11]2[C:21](=[O:22])[CH3:20]

参加物

6

反応物 4

HCID 14798Sodium Hydroxide2 回HCID 24813Phosphorus oxychlorideHCID 31374Dimethylacetamide2 回HCID 706425-Methoxy-2-methylindole

生成物 1

HCID 6048231-(5-Methoxy-2-methyl-1H-indol-3-yl)ethanone収率 67.2%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
0 °C

実験手順

Dimethylacetamide (17.5 ml, 188.4 mmol) is added dropwise with stirring to phosphorous oxychloride (12.9 ml, 138.2 mmol) at 0° C. Stirring is maintained for 45 minutes, at which time the bath is removed and 5-methoxy-2-methylindole (20.25 g, 125.6 mmol) in 15 ml of dimethylacetamide is added dropwise over a period of 75 minutes. The resulting mixture is warmed to 40°-45° C. for 4 hours. The reaction mixture is cooled to 0° C., and 100 g of ice water is added followed by dropwise addition of a solution of sodium hydroxide (50 g) in water (75 ml). The first 1/3 of this sodium hydroxide solution is added slowly and the remainder is added quickly. The exothermic reaction is quickly warmed to boiling for 15 minutes, cooled to room temperature and refrigerated overnight. The resulting crystals are collected by filtration and rinsed four times with water. Recrystallization from ethanol/water gives 17.2 g (67.2%) of pure 1-(5-methoxy-2-methyl-lH-indol-3-yl)ethanone; mp 229.0°-230.5° C.

後処理

  1. temperatureis maintained for 45 minutes, at which time the bath
  2. customis removed
  3. temperatureThe resulting mixture is warmed to 40°-45° C. for 4 hours
  4. additionthe remainder is added quickly
  5. customThe exothermic reaction
  6. temperatureis quickly warmed
  7. temperaturecooled to room temperature and refrigerated overnight
  8. filtrationThe resulting crystals are collected by filtration
  9. washrinsed four times with water
  10. customRecrystallization from ethanol/water

出典と根拠

ORDレコード
ord-19ba101edb19452eb07edd9edb04e239
出典データセット
uspto-grants-1991_12
特許番号
US05075330

関連ノート

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