Benzoyl chloride, 3-nitro- → 5-(3-Nitro-benzoyl)-1,3-dihydro-indol-2-one

HRID 640979

반응식

HRID 640979 반응식
[Al+3].[Cl-].[Cl-].[Cl-].[N+:5]([C:8]1[CH:9]=[C:10]([CH:14]=[CH:15][CH:16]=1)[C:11](Cl)=[O:12])([O-:7])=[O:6].[NH:17]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH2:19][C:18]1=[O:26]>CN(C=O)C>[N+:5]([C:8]1[CH:9]=[C:10]([CH:14]=[CH:15][CH:16]=1)[C:11]([C:22]1[CH:21]=[C:20]2[C:25](=[CH:24][CH:23]=1)[NH:17][C:18](=[O:26])[CH2:19]2)=[O:12])([O-:7])=[O:6]

참가 물질

5

반응물 3

HCID 8495Benzoyl chloride, 3-nitro-HCID 321710OxindoleHCID 6451240Aluminum(III) Chloride

생성물 1

HCID 686984765-(3-Nitro-benzoyl)-1,3-dihydro-indol-2-one

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
0 °C

실험 절차

A 3 L, 3 necked round bottomed flask equipped with a mechanical stirrer, thermocouple and was charged with AlCl3 (256 g, 1.92 mol). The solids were cooled to 0° C. with an ice-H2O bath. DMF (42 ml) was added dropwise over a period of 35 min. The temperature was stirred at 0° C. for 2 h then was warmed to room temperature. The reaction mixture was treated with 3-Nitrobenzoyl chloride (37.3 g, 0.2 mol) and the resulting slurry was heated to 41° C. Subsequently, oxindole (25 g, 0.19 mol) was added over a period of 10 min. The reaction that ensued was exothermic and caused the internal reaction temperature to rise to 60° C. The reaction was heated at 90° C. for 3.5 h. Thin layer chromatographic analysis (Hexanes/ethylacetate 1:1) indicated completion of reaction. The reaction was cooled and ice-H2O (1.5 L) was added dropwise over a period of 1.5 h. The solids were filtered, washed with saturated NaHCO3(aq) (2×300 mL), H2O (300 mL) and Methyl-t-Butyl Ether (500 mL) to yield 5-(3-Nitro-benzoyl)-1,3-dihydro-indol-2-one in quantitative yield (53.63 g, 0.19 mol).

후처리

  1. customA 3 L, 3 necked round bottomed flask equipped with a mechanical stirrer
  2. temperaturethen was warmed to room temperature
  3. temperaturethe resulting slurry was heated to 41° C
  4. customThe reaction
  5. customto rise to 60° C
  6. temperatureThe reaction was heated at 90° C. for 3.5 h
  7. customcompletion of reaction
  8. temperatureThe reaction was cooled
  9. filtrationThe solids were filtered
  10. washwashed with saturated NaHCO3(aq) (2×300 mL), H2O (300 mL) and Methyl-t-Butyl Ether (500 mL)

출처 및 근거

ORD 기록
ord-a0167aecd8794ae5b5209ddbc637086c
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07692005B2

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