Sodium Hydroxide → 1-(1-Methylethyl)-7-(methyloxy)-1H-indole-4-carboxylic acid

HRID 42448Notes

Reaction equation

HRID 42448 reaction equation
[OH-].[Na+].[CH3:3][CH:4]([N:6]1[C:14]2[C:13]([O:15][CH3:16])=[CH:12][CH:11]=[C:10]([C:17]([O:19]C)=[O:18])[C:9]=2[CH:8]=[CH:7]1)[CH3:5]>C(O)C>[CH3:5][CH:4]([N:6]1[C:14]2[C:13]([O:15][CH3:16])=[CH:12][CH:11]=[C:10]([C:17]([OH:19])=[O:18])[C:9]=2[CH:8]=[CH:7]1)[CH3:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67468655Methyl 1-(1-methylethyl)-7-(methyloxy)-1H-indole-4-carboxylate

Product 1

HCID 674686821-(1-Methylethyl)-7-(methyloxy)-1H-indole-4-carboxylic acidYield 92.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Added 1 N sodium hydroxide (6.47 mL, 6.47 mmol) to a solution of methyl 1-(1-methylethyl)-7-(methyloxy)-1H-indole-4-carboxylate (400 mg, 1.618 mmol) in ethanol (30 mL) and heated at reflux for 3 h. The EtOH was removed in vacuo and the residue dissolved in 20 ml of water. Acidifed solution by addition of 1 N HCl and extracted with DCM. the combined DCM extracts were washed with water and brine, dried over MgSO4, filtered and concentrated to give 350 mg of the title compound. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.51 (d, 6H), 4.03 (s, 3H), 5.47 (dt, J=13.39, 6.69 Hz, 2H), 6.70 (d, J=8.34 Hz, 2H), 7.23 (d, J=3.28 Hz, 2H), 7.37 (d, J=3.03 Hz, 2H), 7.99 (d, J=8.34 Hz, 2H). MS (ES) [M+H]+ 234.0.

Workup

  1. temperatureheated
  2. temperatureat reflux for 3 h
  3. customThe EtOH was removed in vacuo
  4. dissolutionthe residue dissolved in 20 ml of water
  5. additionAcidifed solution by addition of 1 N HCl
  6. extractionextracted with DCM
  7. washthe combined DCM extracts were washed with water and brine
  8. dry with materialdried over MgSO4
  9. filtrationfiltered
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-76be913ef9b4493285fa664350b63cae
Source dataset
uspto-grants-2013_09
Patent number
US08536179B2

Reaction notes

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