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

HRID 1515266Notes

Reaction equation

HRID 1515266 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

Commercially available ethyl 7-nitroindole-2-carboxylate (500 mg, 2.14 mmol) was dissolved in a solvent mixture of tetrahydrofuran and water (1:1, 20 mL). Lithium hydroxide hydrate (448 mg, 10.7 mmol) was added thereto, and the mixture was stirred for 8 h at room temperature. 1N-hydrochloric acid solution was added, and the reaction 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 the title compound.

Workup

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

Sources & evidence

ORD record
ord-05dd6076c7764547ab8b1c8c44357adc
Source dataset
uspto-grants-2012_07
Patent number
US08222414B2

Reaction notes

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