Pyridine → 2-chloro-1-phenyl-1H-indole-3-carbaldehyde

HRID 751324

反応式

HRID 751324 の反応式
P(Cl)(Cl)([Cl:3])=O.CN([CH:9]=[O:10])C.[C:11]1([N:17]2[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH2:19][C:18]2=O)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.N1C=CC=CC=1>ClCCl.C(Cl)(Cl)Cl>[Cl:3][C:18]1[N:17]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:25]2[C:20]([C:19]=1[CH:9]=[O:10])=[CH:21][CH:22]=[CH:23][CH:24]=2

参加物

7

反応物 4

HCID 1049PyridineHCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 3147871-Phenyloxindole

生成物 1

HCID 3147932-chloro-1-phenyl-1H-indole-3-carbaldehyde収率 39.25%

試薬・触媒・溶媒 2

HCID 6212Chloroform溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
5 °C

実験手順

Phosphorous oxychloride (50 mL, 538 mmol) is added slowly to a solution of DMF (50 mL) in dichloromethane (50 mL) maintaining the temperature at 5° C. After 30 min, a solution of 1-phenyl-1H-indol-2-one (25 g, 120 mmol) and pyridine (25 mL, 309 mmol) in chloroform (125 mL) is added and the reaction is stirred 48 hr at room temperature. The reaction is poured into ice water (600 mL) and the aqueous layer is separated and extracted with chloroform (3×200 mL). The combined organic layer and extracts is dried, filtered and concentrated. The solid residue is crystallized from ethanol to afford 2-chloro-1-phenyl-1H-indole-3-carboxaldehyde (12.0 g, 39.25% yield) as an orange solid. NMR (CDCl3) 10.21 (1H, s), 8.37 (1H, d), 7.60 (3H, m), 7.41 (2H, m), 7.38 (1H, t), 7.28 (1H, m), 7.10 (1H, d). A second crop (7.5 g, 24.5% yield) is obtained by concentration of the filtrate and chromatography the residue eluting with dichloromethane.

後処理

  1. customthe aqueous layer is separated
  2. extractionextracted with chloroform (3×200 mL)
  3. customThe combined organic layer and extracts is dried
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe solid residue is crystallized from ethanol

出典と根拠

ORDレコード
ord-5472b8fb5bd142229321e325dc561d1f
出典データセット
uspto-grants-2008_07
特許番号
US07405300B2

関連ノート

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