Dimethylformamide → 1-Methyl-2,5-dichloroindole-3-carbaldehyde

HRID 1957199노트

반응식

HRID 1957199 반응식
O=P(Cl)(Cl)[Cl:3].[CH3:6][N:7]([CH:9]=O)[CH3:8].CN1C2[C:15](=[CH:16][C:17]([Cl:21])=[CH:18][CH:19]=2)[CH2:14][C:13]1=[O:22].C([O-])(O)=O.[Na+]>ClCCl.N1C=CC=CC=1>[CH3:8][N:7]1[C:6]2[C:15](=[CH:16][C:17]([Cl:21])=[CH:18][CH:19]=2)[C:14]([CH:13]=[O:22])=[C:9]1[Cl:3]

참가 물질

7

반응물 4

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 516892Sodium BicarbonateHCID 109761125-chloro-1-methyl-2,3-dihydro-1H-indol-2-one

생성물 1

HCID 190689371-Methyl-2,5-dichloroindole-3-carbaldehyde

시약·촉매·용매 2

HCID 1049Pyridine용매HCID 6344Dichloromethane용매2회

실험 절차

POCl3 (6 ml) was added dropwise to a mixture of dry DMF (5.9 ml) and dichloromethane (5.9 ml) kept at 0° C. 1-Methyl-5-chloro-1,3-dihydroindol-2-one (4.0 g) dissolved in dichloromethane (20 ml) and pyridine (2.9 ml) was added dropwise at 0° C. over a period of 30 min. Subsequent stirring at room temperature for 3h. The mixture was poured onto icewater (500 ml) neutralized with NaHCO3 whereafter the mixture was stirred overnight. The precipitate was filtered off, washed with water and dried. The crude material (4.45 g) was recrystallized from ethanol yielding 1.27 g (25.4%) of (45). M.p. 165°-167° C.

후처리

  1. customkept at 0° C
  2. additionThe mixture was poured onto icewater (500 ml)
  3. stirringwas stirred overnight
  4. filtrationThe precipitate was filtered off
  5. washwashed with water
  6. customdried
  7. customThe crude material (4.45 g) was recrystallized from ethanol yielding 1.27 g (25.4%) of (45)

출처 및 근거

ORD 기록
ord-8e1f83e0ed46484696b0288782d34c31
출처 데이터셋
uspto-grants-1998_07
특허 번호
US05783575

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