Ethanol → ethyl 7-nitro-2-phenyl-1H-indole-5-carboxylate

HRID 1466497Notes

Reaction equation

HRID 1466497 reaction equation
[C:1]1([C:7]2[NH:8][C:9]3[C:14]([CH:15]=2)=[CH:13][C:12]([C:16]([OH:18])=[O:17])=[CH:11][C:10]=3[N+:19]([O-:21])=[O:20])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.S(=O)(=O)(O)O.[OH-].[Na+].[CH2:29](O)[CH3:30]>>[CH2:29]([O:17][C:16]([C:12]1[CH:13]=[C:14]2[C:9](=[C:10]([N+:19]([O-:21])=[O:20])[CH:11]=1)[NH:8][C:7]([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)=[CH:15]2)=[O:18])[CH3:30]

Participants

5

Reactant 4

HCID 702EthanolHCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 684765287-Nitro-2-phenyl-1h-indole-5-carboxylic acid

Product 1

HCID 68474038ethyl 7-nitro-2-phenyl-1H-indole-5-carboxylateYield 95%

Conditions

Temperature
50 °C

Procedure

2-Phenyl-7-nitro-1H-indole-5-carboxylic acid (14.1 g, 50 mmol) prepared in Preparation 30 was dissolved in ethanol (40 mL). Conc. sulfuric acid (10 mL) was added thereto, and the mixture was stirred for 2 h at 50° C. After completion of the reaction, 1N NaOH was added to the reaction mixture, which was then extracted with EtOAc, dried over anhydrous magnesium sulfate, and filtered. The solvent was removed under reduced pressure, and the residue was recrystallized from EtOAc and hexane to give the title compound (14.1 g, Yield 95%).

Workup

  1. additionwas added to the reaction mixture, which
  2. extractionwas then extracted with EtOAc
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customThe solvent was removed under reduced pressure
  6. customthe residue was recrystallized from EtOAc and hexane

Sources & evidence

ORD record
ord-7ca302c672684621975139d9d400f64c
Source dataset
uspto-grants-2015_04
Patent number
US09000028B2

Reaction notes

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