Lithium Hydroxide → (2-Chloro-6-dimethylaminomethyl-naphthalen-1-yl)-acetic acid

HRID 639197Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 639197
C([O:3][C:4](=[O:21])[CH2:5][C:6]1[C:15]2[C:10](=[CH:11][C:12]([CH2:16][N:17]([CH3:19])[CH3:18])=[CH:13][CH:14]=2)[CH:9]=[CH:8][C:7]=1[Cl:20])C.[OH-].[Li+].OS([O-])(=O)=O.[Na+]>O1CCOCC1.O>[Cl:20][C:7]1[CH:8]=[CH:9][C:10]2[C:15](=[CH:14][CH:13]=[C:12]([CH2:16][N:17]([CH3:18])[CH3:19])[CH:11]=2)[C:6]=1[CH2:5][C:4]([OH:21])=[O:3]

Komponenten

6

Edukt 3

HCID 3939Lithium HydroxideHCID 516919Sodium BisulfateHCID 68704219(2-Chloro-6-dimethylaminomethyl-naphthalen-1-yl)-acetic acid ethyl ester

Produkt 1

HCID 68706916(2-Chloro-6-dimethylaminomethyl-naphthalen-1-yl)-acetic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittel2×HCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

(2-Chloro-6-dimethylaminomethyl-naphthalen-1-yl)-acetic acid ethyl ester (223 mg, 0.73 mmol) is dissolved in dioxane (2.6 ml). Water (0.96 ml) and lithium hydroxide (21 mg, 0.88 mmol) are then added, and the reaction mixture is warmed to 60° C. for 4 h. HPLC analysis indicates complete conversion of starting material. The reaction is diluted with water, adjusted to pH 6-7 by addition of 1 M aqueous NaHSO4, and extracted with EtOAc. The water layer is then concentrated, and the solid residue is repeatedly extracted with MeOH to yield pure title compound. ES+-MS: 278.3, 280.1 [M+H]+.

Aufarbeitung

  1. extractionextracted with EtOAc
  2. concentrationThe water layer is then concentrated
  3. extractionthe solid residue is repeatedly extracted with MeOH

Quellen und Nachweise

ORD-Eintrag
ord-17c96eb9efed46f8a778ade623572b59
Quelldatensatz
uspto-grants-2010_04
Patentnummer
US07691861B2

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