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

HRID 1957199ノート

反応式

HRID 1957199 の反応式
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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 1049Pyridine溶媒HCID 6344Dichloromethane溶媒2 回

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-8e1f83e0ed46484696b0288782d34c31
出典データセット
uspto-grants-1998_07
特許番号
US05783575

反応ノート

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