Hydrochloric Acid → 4-(3-Formyl-6-nitroindol-1-yl)benzoic acid ethyl ester

HRID 1258218노트

반응식

HRID 1258218 반응식
[CH2:1]([O:3][C:4](=[O:23])[C:5]1[CH:10]=[CH:9][C:8]([N:11]2[C:19]3[C:14](=[CH:15][CH:16]=[C:17]([N+:20]([O-:22])=[O:21])[CH:18]=3)[CH:13]=[CH:12]2)=[CH:7][CH:6]=1)[CH3:2].P(Cl)(Cl)(Cl)=O.[OH-].[Na+].Cl.CN(C)[CH:34]=[O:35]>>[CH2:1]([O:3][C:4](=[O:23])[C:5]1[CH:6]=[CH:7][C:8]([N:11]2[C:19]3[C:14](=[CH:15][CH:16]=[C:17]([N+:20]([O-:22])=[O:21])[CH:18]=3)[C:13]([CH:34]=[O:35])=[CH:12]2)=[CH:9][CH:10]=1)[CH3:2]

참가 물질

6

반응물 5

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 584372194-(6-Nitroindol-1-yl)benzoic acid ethyl ester

생성물 1

HCID 866396014-(3-Formyl-6-nitroindol-1-yl)benzoic acid ethyl ester

반응 조건

온도
70 °C

실험 절차

To a solution of 4-(6-nitroindol-1-yl)benzoic acid ethyl ester (0.53 g) in N,N-dimethylformamide (6 mL) was added phosphoryl chloride (0.31 g) under ice cooling and this mixture was stirred at 70° C. overnight. After cooling to ambient temperature, to this reaction mixture was added 2 mol/L aqueous sodium hydroxide solution and this mixture was stirred at 30 minutes. This reaction mixture was poured into 1 mol/L hydrochloric acid, and the precipitated solid was collected by filtration, and washed with water and n-hexane, and dried under reduced pressure at 40° C. to give 4-(3-formyl-6-nitroindol-1-yl)benzoic acid ethyl ester (0.46 g). To a solution of this aldehyde (0.46 g) in tetrahydrofuran (10 mL) were added hydroxylamine hydrochloride (0.19 g) and pyridine (0.43 g) at room temperature, and this mixture was stirred at 80° C. for 8 hours. To this reaction mixture was added acetic anhydride (0.42 g) at 80° C., this mixture was stirred at same temperature overnight. After cooling to ambient temperature, to this reaction mixture was added 1 mol/L hydrochloric acid, and the precipitated solid was collected by filtration. This solid was washed with water, n-hexane and diethyl ether to give the title compound (0.13 g).

후처리

  1. temperatureAfter cooling to ambient temperature, to this reaction mixture
  2. stirringthis mixture was stirred at 30 minutes
  3. filtrationthe precipitated solid was collected by filtration
  4. washwashed with water and n-hexane
  5. customdried under reduced pressure at 40° C.

출처 및 근거

ORD 기록
ord-6b06f9dbe3e24737aff4dd1b9d7244fe
출처 데이터셋
uspto-grants-2013_06
특허 번호
US08466152B2

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