Hydrochloric Acid → HCID 21194769, compound

HRID 1067853Notes

Reaction equation

HRID 1067853 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[C:6]([C:19]([F:22])([F:21])[F:20])[CH:7]=[CH:8][C:9]=2[O:11][CH2:12][CH2:13][N:14]2[CH:18]=[CH:17][CH:16]=[CH:15]2)[CH:4]=[C:3]1[C:23]([O:25]CC)=[O:24].Cl>C(O)C.O1CCCC1.[OH-].[Na+]>[CH3:1][N:2]1[C:10]2[C:5](=[C:6]([C:19]([F:22])([F:20])[F:21])[CH:7]=[CH:8][C:9]=2[O:11][CH2:12][CH2:13][N:14]2[CH:18]=[CH:17][CH:16]=[CH:15]2)[CH:4]=[C:3]1[C:23]([OH:25])=[O:24]

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 21194584HCID 21194584, compound

Product 1

HCID 21194769HCID 21194769, compoundYield 60.7%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolventHCID 14798Sodium HydroxideSolvent

Procedure

After 1.94 g (5.10 mmol) of ethyl 1-methyl-7-[2-(1H-pyrrol-1-yl)ethoxy]-4-trifluoromethyl-2-indolecarboxylate was dissolved in a mixture of 100 ml of ethanol and 50 ml of tetrahydrofuran, 10 ml of 3.75 N sodium hydroxide was added thereto. The mixture was stirred at room temperature for an hour. After completion of the reaction, the mixture was rendered acidic with 2 N hydrochloric acid and concentrated under reduced pressure. To the concentrate was added 100 ml of water. The mixture was then extracted with ethyl acetate. The extract was washed with water and dried over magnesium sulfate. The solvent was distilled off under reduced pressure. Crystallization of the resulting residue from chloroform/ethyl acetate gave 1.09 g of 1-methyl-7-[2-(1H-pyrrol-1-yl)ethoxy]-4-trifluoromethyl-2-indolecarboxylic acid.

Workup

  1. additionwas added
  2. customAfter completion of the reaction
  3. concentrationconcentrated under reduced pressure
  4. additionTo the concentrate was added 100 ml of water
  5. extractionThe mixture was then extracted with ethyl acetate
  6. washThe extract was washed with water
  7. dry with materialdried over magnesium sulfate
  8. distillationThe solvent was distilled off under reduced pressure
  9. customCrystallization of the resulting residue from chloroform/ethyl acetate

Sources & evidence

ORD record
ord-4a0f5a661ffe4614a42470eefc86461b
Source dataset
uspto-grants-2001_06
Patent number
US06248772B1

Reaction notes

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