Sodium Hydroxide → 7-Methyl-1-(1-methylethyl)-1H-indole-4-carboxylic acid

HRID 516702Notes

Reaction equation

HRID 516702 reaction equation
[CH3:1][C:2]1[C:10]2[N:9]([CH:11]([CH3:13])[CH3:12])[CH:8]=[CH:7][C:6]=2[C:5]([C:14]([O:16]C)=[O:15])=[CH:4][CH:3]=1.[OH-].[Na+]>C(O)C>[CH3:1][C:2]1[C:10]2[N:9]([CH:11]([CH3:13])[CH3:12])[CH:8]=[CH:7][C:6]=2[C:5]([C:14]([OH:16])=[O:15])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67468444methyl 7-methyl-1-(1-methylethyl)-1H-indole-4-carboxylate

Product 1

HCID 674672047-Methyl-1-(1-methylethyl)-1H-indole-4-carboxylic acidYield 80.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of methyl 7-methyl-1-(1-methylethyl)-1H-indole-4-carboxylate (137 mg, 0.592 mmol) in ethanol (30 mL) was added 1 N sodium hydroxide (2.369 mL, 2.369 mmol). The mixture was heated at reflux for 2 h, at which time it was concentrated. The residue was dissolved in water (20 mL) and acidified by addition of 1 N HCl. The mixture was extracted with DCM (4×30 mL) and the combined extracts and washed with water and brine, dried over MgSO4, filtered and concentrated to give 104 mg of the title compound. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.55 (d, 6H), 2.82 (s, 3H), 5.11-5.28 (m, 1H), 7.00 (d, J=7.83 Hz, 1H), 7.31 (d, J=3.54 Hz, 1H), 7.44 (d, J=3.28 Hz, 1H), 7.89 (d, J=7.58 Hz, 1H). MS(ES) [M+H]+ 218.3.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 2 h, at which time it
  3. concentrationwas concentrated
  4. dissolutionThe residue was dissolved in water (20 mL)
  5. additionacidified by addition of 1 N HCl
  6. extractionThe mixture was extracted with DCM (4×30 mL)
  7. washthe combined extracts and washed with water and brine
  8. dry with materialdried over MgSO4
  9. filtrationfiltered
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-7413be56b6e24dc5a1abf80712ea5cb3
Source dataset
uspto-grants-2015_08
Patent number
US09114141B2

Reaction notes

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