Methanol → Methyl 3-amino-4-methoxybenzoate hydrochloride

HRID 131270

Reaktionsgleichung

Reaktionsgleichung von HRID 131270
S(Cl)([Cl:3])=O.[NH2:5][C:6]1[CH:7]=[C:8]([CH:12]=[CH:13][C:14]=1[O:15][CH3:16])[C:9]([OH:11])=[O:10].[CH3:17]O>>[ClH:3].[NH2:5][C:6]1[CH:7]=[C:8]([CH:12]=[CH:13][C:14]=1[O:15][CH3:16])[C:9]([O:11][CH3:17])=[O:10]

Komponenten

4

Edukt 3

HCID 887MethanolHCID 178233-Amino-4-methoxybenzoic acidHCID 24386Thionyl Chloride

Produkt 1

HCID 69298967Methyl 3-amino-4-methoxybenzoate hydrochlorideAusbeute 96 %

Reaktionsbedingungen

Temperatur
-20 °C

Versuchsvorschrift

Thionyl chloride (8.7 mL) is added dropwise to methanol (90 mL) at −30° C. under argon gas atmosphere over a period of 15 minutes and a mixture is stirred at −20° C. for 30 minutes. To the mixture is added 3-amino-4-methoxybenzoic acid (5.0 g) and the solution is stirred at the same temperature for 15 minutes and at room temperature for 3 days. The reaction mixture is concentrated in vacuo and the resultant crystals are washed with methanol/ether to give methyl 3-amino-4-methoxybenzoate hydrochloride (6.25 g, yield; 96%) as colorless crystals. M.p. 213-215° C., MS (APCI) m/z: 182 [M+H]+

Aufarbeitung

  1. stirringthe solution is stirred at the same temperature for 15 minutes and at room temperature for 3 days
  2. concentrationThe reaction mixture is concentrated in vacuo
  3. washthe resultant crystals are washed with methanol/ether

Quellen und Nachweise

ORD-Eintrag
ord-9e874705f6394bc8806f3d6634579f66
Quelldatensatz
uspto-grants-2008_06
Patentnummer
US07384952B2

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