Hydrochloric Acid → 4-(3-Isopropyl-1H-indol-5-yloxy)-3,5-bis-trifluoromethyl-cinnamic acid

HRID 1007509Notes

Reaction equation

HRID 1007509 reaction equation
[CH:1]([C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([O:13][C:14]3[C:26]([C:27]([F:30])([F:29])[F:28])=[CH:25][C:17]([CH:18]=[CH:19][C:20]([O:22]CC)=[O:21])=[CH:16][C:15]=3[C:31]([F:34])([F:33])[F:32])[CH:11]=2)[NH:6][CH:5]=1)([CH3:3])[CH3:2].[OH-].[Na+].Cl.C(OCC)(=O)C>O1CCOCC1>[CH:1]([C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([O:13][C:14]3[C:26]([C:27]([F:28])([F:29])[F:30])=[CH:25][C:17]([CH:18]=[CH:19][C:20]([OH:22])=[O:21])=[CH:16][C:15]=3[C:31]([F:34])([F:32])[F:33])[CH:11]=2)[NH:6][CH:5]=1)([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 86587749Ethyl 4-(3-isopropyl-1H-indol-5-yloxy)-3,5-bis-trifluoromethyl-cinnamate

Product 1

HCID 853318014-(3-Isopropyl-1H-indol-5-yloxy)-3,5-bis-trifluoromethyl-cinnamic acid

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

0.23 g (0.46 mmol) of ethyl cinnamate derivative from Example 13 are dissolved in 10 ml of dioxane, 4 ml of 1 molar sodium hydroxide solution are added and the mixture is stirred for 5 hours at room temperature. The reaction solution is acidified to pH 4 using 1N hydrochloric acid, treated with ethyl acetate and the aqueous phase is extracted a further two times with ethyl acetate. The combined organic phases are washed with sodium chloride solution, dried over sodium sulphate, filtered, concentrated and dried overnight in a high vacuum.

Workup

  1. extractionthe aqueous phase is extracted a further two times with ethyl acetate
  2. washThe combined organic phases are washed with sodium chloride solution
  3. dry with materialdried over sodium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customdried overnight in a high vacuum

Sources & evidence

ORD record
ord-7bbcdc45c63f47e299dc5667655277c0
Source dataset
uspto-grants-2004_09
Patent number
US06794406B2

Reaction notes

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