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

HRID 1802810Notes

Reaction equation

HRID 1802810 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]CC)=[O:14])=[CH:9]2)([O-:3])=[O:2].O.[OH-].[Li+].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 168937Lithium hydroxide, monohydrateHCID 250407Ethyl 7-nitro-1H-indole-2-carboxylate

Product 1

HCID 814097-nitro-1H-indole-2-carboxylic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 7-nitroindole-2-carboxylate (500 mg, 2.14 mmol) was dissolved in a solvent mixture of tetrahydrofuran and water (1:1, 20 ml), and lithium hydroxide hydrate (448 mg, 10.7 mmol) was added. The mixture was stirred for 8 h at room temperature, and 1N-hydrochloric acid solution was added thereto. The mixture was extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate and filtered. The filtrate was distilled under reduced pressure to give 7-nitro-1H-indole-2-carboxylic acid.

Workup

  1. additionwas added
  2. extractionThe mixture was extracted with ethyl acetate
  3. dry with materialThe extract was dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. distillationThe filtrate was distilled under reduced pressure

Sources & evidence

ORD record
ord-baa93d251c7943ee9ceb53185f92771c
Source dataset
uspto-grants-2013_01
Patent number
US08349885B2

Reaction notes

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