Ethanol → 5-Nitroindole-2-carboxylic acid

HRID 450718Notes

Reaction equation

HRID 450718 reaction equation
C([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([N+:15]([O-:17])=[O:16])=[CH:10][CH:9]=2)=[O:5])C.C(O)C>>[N+:15]([C:11]1[CH:12]=[C:13]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:4]([OH:5])=[O:3])=[CH:14]2)([O-:17])=[O:16]

Participants

3

Reactant 2

HCID 702EthanolHCID 280312Ethyl 5-nitro-1H-indole-2-carboxylate

Product 1

HCID 3512915-Nitroindole-2-carboxylic acidYield 98%

Procedure

To a solution of ethyl-5-nitro-1H-indole-2-carboxylate (22.7 g, 96.83 mg) in ethanol (EtOH) (150 ml) sodium hydroxide (11.62 g, 290.5 mmol) was added. The mixture was stirred at room temperature for 16 h. During this time a brown solid formed. After evaporation of the solvent under reduced pressure the residue was suspended in water and HCl was added. The color of the precipitate changed from brown to yellow. After filtration the residue was washed with water and dried in a vacuum oven at 50° C. to give the product as a brown powder (19.53 g, 98%).

Workup

  1. customDuring this time a brown solid formed
  2. customAfter evaporation of the solvent under reduced pressure the residue
  3. additionHCl was added
  4. filtrationAfter filtration the residue
  5. washwas washed with water
  6. customdried in a vacuum oven at 50° C.

Sources & evidence

ORD record
ord-21ea59f7972d49c29cc9fd0fb6a55922
Source dataset
uspto-grants-2013_07
Patent number
US08486984B2

Reaction notes

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