Hydrochloric Acid → 7-nitro-1H-indole-2-carboxylic acid

HRID 1876309Notes

Reaction equation

HRID 1876309 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:12]=1[NH:11][C:10]([C:13]([O:15]C)=[O:14])=[CH:9]2)([O-:3])=[O:2].[OH-].[Na+].Cl>O1CCCC1.O>[N+:1]([C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:12]=1[NH:11][C:10]([C:13]([OH:15])=[O:14])=[CH:9]2)([O-:3])=[O:2]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 18550960Methyl 7-nitro-1h-indole-2-carboxylate

Product 1

HCID 814097-nitro-1H-indole-2-carboxylic acidYield 99%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Methyl 7-nitroindole-2-carboxylate (13 g, 59 mmol) prepared in Preparation 8 was dissolved in a solvent mixture of tetrahydrofuran and water (1:1, 300 ml), and 1N aqueous sodium hydroxide solution (180 ml, 177 mmol) was added thereto. The mixture was stirred for 3 h at room temperature, excess 6N hydrochloric acid solution was added, and the mixture was extracted with ethyl acetate. The extract was washed with saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and filtered. The filtrate was distilled under reduced pressure to give 7-nitro-1H-indole-2-carboxylic acid (12 g, Yield 99%).

Workup

  1. additionwas added
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with saturated sodium chloride solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. distillationThe filtrate was distilled under reduced pressure

Sources & evidence

ORD record
ord-d86e26509b3d444f9cbc1746388a21f3
Source dataset
uspto-grants-2012_11
Patent number
US08309586B2

Reaction notes

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