Water → 6-bromo-1-isopropyl-3-methyl-1H-indole-4-carboxylic acid

HRID 42506Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 42506
[Br:1][C:2]1[CH:3]=[C:4]([C:15]([O:17]C)=[O:16])[C:5]2[C:6]([CH3:14])=[CH:7][N:8]([CH:11]([CH3:13])[CH3:12])[C:9]=2[CH:10]=1.[OH-].[Na+].O>C(O)C>[Br:1][C:2]1[CH:3]=[C:4]([C:15]([OH:17])=[O:16])[C:5]2[C:6]([CH3:14])=[CH:7][N:8]([CH:11]([CH3:13])[CH3:12])[C:9]=2[CH:10]=1

Komponenten

5

Edukt 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 67464634methyl 6-bromo-1-isopropyl-3-methyl-1H-indole-4-carboxylate

Produkt 1

HCID 674686786-bromo-1-isopropyl-3-methyl-1H-indole-4-carboxylic acidAusbeute 89,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To a stirred solution of methyl 6-bromo-1-isopropyl-3-methyl-1H-indole-4-carboxylate (24 g, 77.4 mmol) in ethanol (400 mL) was added sodium hydroxide (4.02 g, 100.6 mmol), water (11 mL) and the mixture was stirred at reflux condition for 6 h. Ethanol was distilled off and residue was diluted with water, extracted with ethylacetate (40 mL) adjusted aqueous layer to PH-3 with 1N HCl and extracted with ethyl acetate (3×250 mL), finally organic layer was washed with brine solution, dried over anhydrous Na2SO4 and concentrated. The crude was washed with pet ether, filtered the solid and dried to afford desired product 6-bromo-1-isopropyl-3-methyl-1H-indole-4-carboxylic acid (20.6 g, 89.8%).

Aufarbeitung

  1. temperatureat reflux condition for 6 h
  2. distillationEthanol was distilled off
  3. additionresidue was diluted with water
  4. extractionextracted with ethylacetate (40 mL)
  5. extractionextracted with ethyl acetate (3×250 mL), finally organic layer
  6. washwas washed with brine solution
  7. dry with materialdried over anhydrous Na2SO4
  8. concentrationconcentrated
  9. washThe crude was washed with pet ether
  10. filtrationfiltered the solid
  11. customdried

Quellen und Nachweise

ORD-Eintrag
ord-5688b33536e4441d973ee67297f2ee28
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08536179B2

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