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

HRID 1195899

반응식

HRID 1195899 반응식
P(Cl)(Cl)(Cl)=O.[CH3:6][O:7][C:8]1[C:16]2C(=[CH:12][CH:13]=[CH:14][CH:15]=2)N[C:9]=1[CH3:17].[OH-:18].[Na+].[CH3:20][C:21]([N:23]([CH3:25])C)=O>O>[CH3:6][O:7][C:8]1[CH:16]=[C:15]2[C:25](=[CH:17][CH:9]=1)[NH:23][C:21]([CH3:20])=[C:14]2[C:13](=[O:18])[CH3:12]

참가 물질

6

반응물 4

HCID 14798Sodium Hydroxide2회HCID 24813Phosphorus oxychlorideHCID 31374Dimethylacetamide2회HCID 53764995HCID 53764995, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
0 °C

실험 절차

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 -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-1H-indol-3- yl)ethanone; mp 229.0°-230.5° C.

후처리

  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

출처 및 근거

ORD 기록
ord-71850abaab6c45a6bc4cd6f38c03d618
출처 데이터셋
uspto-grants-1992_05
특허 번호
US05112846

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