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

HRID 62347Notes

Reaction equation

HRID 62347 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. Acidified 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. additionAcidified 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-dbf39f8787584d429fe26e04b8559d3e
Source dataset
uspto-grants-2016_09
Patent number
US09446041B2

Reaction notes

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