Sodium Hydroxide → 178053-59-3

HRID 1067762Notes

Reaction equation

HRID 1067762 reaction equation
[CH:1]([N:4]1[C:12]2[C:7](=[CH:8][C:9]([C:13]([O:15]C(C)C)=[O:14])=[CH:10][CH:11]=2)[CH:6]=[CH:5]1)([CH3:3])[CH3:2].[OH-].[Na+]>C(O)C>[CH:1]([N:4]1[C:12]2[C:7](=[CH:8][C:9]([C:13]([OH:15])=[O:14])=[CH:10][CH:11]=2)[CH:6]=[CH:5]1)([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 10658018HCID 10658018, compound

Product 1

HCID 21194436178053-59-3Yield 109.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2.20 g (8.97 mmol) of isopropyl 1-isopropyl-5-indolecarboxylate, 100 ml of 2N sodium hydroxide solution and 100 ml of ethanol was refluxed for an hour. The solvent was then distilled off under reduced pressure. Thereafter water was added to the residue and the resulting mixture was acidified with conc. hydrochloric acid. The precipitated solid was filtered and dried under reduced pressure to give 2.00 g of crude 1-isopropyl-5-indole-carboxylic acid. The reaction was carried out in a manner similar to Reference Example 4 using 2.00 g of the crude 1-isopropyl-5-indolecarboxylic acid, 0.44 g (11.1 mmol) of 60% sodium hydride, 2.87 g (20.2 mmol) of methyl iodide and 50 ml of dimethyl-formamide. Thus, 1.64 g (84.2%; yield based on isopropyl 1-isopropyl-5-indolecarboxylic acid) was obtained.

Workup

  1. temperaturewas refluxed for an hour
  2. distillationThe solvent was then distilled off under reduced pressure
  3. additionThereafter water was added to the residue
  4. filtrationThe precipitated solid was filtered
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-8ac954a7dc734fb38d3c8d6cf4ef90be
Source dataset
uspto-grants-2001_06
Patent number
US06248772B1

Reaction notes

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