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

HRID 593827Notes

Reaction equation

HRID 593827 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 1N 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. Acidified solution by addition of 1N 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. additionAcidified solution by addition of 1N 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-34ee3ff3d097476783016cf1a0a67e40
Source dataset
uspto-grants-2016_01
Patent number
US09242962B2

Reaction notes

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