Sodium Hydroxide → 5-chloro-1-(3-methylbenzyl)-1H-indole-2-carboxylic acid

HRID 2242346

Reaktionsgleichung

Reaktionsgleichung von HRID 2242346
[OH-].[Na+].C([O:5][C:6]([C:8]1[N:9]([CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([CH3:25])[CH:20]=2)[C:10]2[C:15]([CH:16]=1)=[CH:14][C:13]([Cl:17])=[CH:12][CH:11]=2)=[O:7])C>C(O)C>[Cl:17][C:13]1[CH:14]=[C:15]2[C:10](=[CH:11][CH:12]=1)[N:9]([CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([CH3:25])[CH:20]=1)[C:8]([C:6]([OH:7])=[O:5])=[CH:16]2

Komponenten

4

Edukt 2

HCID 14798Sodium HydroxideHCID 68547855HCID 68547855, Verbindung

Produkt 1

HCID 685441795-chloro-1-(3-methylbenzyl)-1H-indole-2-carboxylic acidAusbeute 96,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
45 °C

Versuchsvorschrift

A solution of 4M aqueous sodium hydroxide (0.29 ml) was added to a solution of 5-chloro-1-(3-methylbenzyl)-1H-indole-2-carboxylic acid ethyl ester (2.90 g, 8.85 mmol) in ethanol (30 ml) and the reaction heated at 45° C. for 3 h. After concentrating the mixture to 5 ml, a solution of 2M aqueous HCl (2 ml) was added to precipitate the product as a pale solid which was filtered, washed with water (3×30 ml) and dried under vacuum, to afford 5-chloro-1-(3-methylbenzyl)-1H-indole-2-carboxylic acid (2.57 g, 89%).

Aufarbeitung

  1. concentrationAfter concentrating the mixture to 5 ml
  2. additiona solution of 2M aqueous HCl (2 ml) was added
  3. customto precipitate the product as a pale solid which
  4. filtrationwas filtered
  5. washwashed with water (3×30 ml)
  6. customdried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-3645d728a7ed4f43ae7c23793e6c9011
Quelldatensatz
uspto-grants-2010_03
Patentnummer
US07671080B2

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