Lithium Hydroxide → 5-Nitroindole-2-carboxylic acid

HRID 1824988Notes

Reaction equation

HRID 1824988 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][C:8]([C:13]([O:15]CC)=[O:14])=[CH:7]2)([O-:3])=[O:2].[OH-].[Li+]>CO.C1COCC1>[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][C:8]([C:13]([OH:15])=[O:14])=[CH:7]2)([O-:3])=[O:2]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 280312Ethyl 5-nitro-1H-indole-2-carboxylate

Product 1

HCID 3512915-Nitroindole-2-carboxylic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
90 °C

Procedure

16.5 g (66.93 mmol) of ethyl 5-nitroindole-2-carboxylate are dissolved in 200 ml each of methanol and THF, and 67 ml (133.85 mmol) of lithium hydroxide solution are added. The mixture is heated at 90° C. for half an hour. After cooling, the mixture is, for work-up, diluted and extracted with aqueous hydrochloric acid and ethyl acetate. The organic phase is washed with sat. sodium chloride solution, dried with sodium sulphate, filtered and dried under reduced pressure.

Workup

  1. temperatureAfter cooling
  2. additiondiluted
  3. extractionextracted with aqueous hydrochloric acid and ethyl acetate
  4. washThe organic phase is washed with sat. sodium chloride solution
  5. dry with materialdried with sodium sulphate
  6. filtrationfiltered
  7. customdried under reduced pressure

Sources & evidence

ORD record
ord-5806e2f4642e4f378858ca8c7f2f0d47
Source dataset
uspto-grants-2006_05
Patent number
US07045544B2

Reaction notes

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