Ethanol → 1-Isopropyl-6-(trifluoromethyl)-1H-indole-4-carboxylic acid

HRID 42418Notes

Reaction equation

HRID 42418 reaction equation
[CH3:1][CH:2]([N:4]1[C:12]2[CH:11]=[C:10]([C:13]([F:16])([F:15])[F:14])[CH:9]=C(C#N)[C:7]=2[CH:6]=[CH:5]1)[CH3:3].[OH-:19].[Na+].[CH2:21]([OH:23])[CH3:22]>>[CH:2]([N:4]1[C:12]2[CH:11]=[C:10]([C:13]([F:16])([F:15])[F:14])[CH:9]=[C:22]([C:21]([OH:19])=[O:23])[C:7]=2[CH:6]=[CH:5]1)([CH3:3])[CH3:1]

Participants

4

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 674661341-Isopropyl-6-(trifluoromethyl)-1H-indole-4-carbonitrile

Product 1

HCID 674642241-Isopropyl-6-(trifluoromethyl)-1H-indole-4-carboxylic acidYield 86%

Procedure

To a solution of 1-(1-methylethyl)-6-(trifluoromethyl)-1H-indole-4-carbonitrile (180 mg, 0.714 mmol) in ethanol (5 mL) was added 10% sodium hydroxide (5 mL, 0.714 mmol), and the mixture was heated at reflux overnight. The mixture was concentrated to remove EtOH and the aqueous phase was acidified using 1N HCl to ˜pH 4. The precipitate was collected by filtration and dried under high vacuum to give the title compound (167 mg, 86%) as brown solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.43-1.60 (m, 6H), 4.96-5.13 (m, 1H), 7.11 (d, J=3.28 Hz, 1H), 7.89-8.05 (m, 2H), 8.25 (s, 1H), 13.15 (br. s., 1H). MS: (M+H)+=272.0.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux overnight
  3. concentrationThe mixture was concentrated
  4. customto remove EtOH
  5. filtrationThe precipitate was collected by filtration
  6. customdried under high vacuum

Sources & evidence

ORD record
ord-0fa96a248b0c40f195088528806abb37
Source dataset
uspto-grants-2013_09
Patent number
US08536179B2

Reaction notes

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