Methanol → Methyl 2-(3-aminophenyl)acetate hydrochloride

HRID 129192Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 129192
[NH2:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]([OH:11])=[O:10])[CH:5]=[CH:6][CH:7]=1.S(Cl)([Cl:14])=O.[CH3:16]O>>[ClH:14].[CH3:16][O:10][C:9](=[O:11])[CH2:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([NH2:1])[CH:3]=1

Komponenten

4

Edukt 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 571807(3-Aminophenyl)acetic acid

Produkt 1

HCID 44119610Methyl 2-(3-aminophenyl)acetate hydrochlorideAusbeute 96,8 %

Versuchsvorschrift

A suspension of 3-amino phenylacetic acid (5.0 g, 33 mmol) in methanol (50 ml) at 0° C. under argon was slowly treated with thionyl chloride (19.4 g, 165 mmol). After completion of addition, the reaction mixture was allowed to warm up to room temperature and stirred for 16 hours. The solvent was evaporated and the residue was triturated with ethyl ether to give 3-amino phenylacetic acid methylester hydrochloride (5.3 g, 96.8% ) as a colorless solid. 1H NMR (CDCl3) δ10.6 (s, 2H), 7.42 (m, 4H), 3.68 (s, 3H), 3.66 (s, 2H); 13C NMR (CDCl3) 172.5, 137.3, 133.1, 131.2, 130.8, 125.9, 123.7, 53.5, 41.5.

Aufarbeitung

  1. additionAfter completion of addition
  2. customThe solvent was evaporated
  3. customthe residue was triturated with ethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-f3abd5d4a5c4470ebd857ce587a7206a
Quelldatensatz
uspto-grants-1995_11
Patentnummer
US05466817

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