Methanol → Methyl 3-aminobenzoate hydrochloride

HRID 37775

Reaktionsgleichung

Reaktionsgleichung von HRID 37775
[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=[O:6].S(Cl)([Cl:13])=O.[CH3:15]O>>[ClH:13].[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([O:7][CH3:15])=[O:6]

Komponenten

4

Edukt 3

HCID 887MethanolHCID 74193-Aminobenzoic AcidHCID 24386Thionyl Chloride

Produkt 1

HCID 12238913Methyl 3-aminobenzoate hydrochlorideAusbeute 98 %

Versuchsvorschrift

To a suspension of 3-aminobenzoic acid (1.03 g mg, 7.52 mmol) in MeOH (80 mL) at 0° C. was added dropwise thionyl chloride (5 mL). The resulting solution was allowed to stir for 16 h before the solvent was removed by evaporation and the product precipitated with diethyl ether. The diethyl ether was removed by evaporation to yield the title compound (1.38 g, 7.38 mmol, 98%) as a white solid. Mp 176-178° C. 1H NMR (D2O, 300 MHz): δ 7.75 (dt, J=1.8, 3.3, 7.2 Hz, 1H, ArH); 7.71 (m, 1H, ArH); 7.42 (m, 1H, ArH); 7.37 (m, 1H, ArH); 3.66 (s, 31H, OCH3). Mass Spectrum (C1) m/z 152 (100%) [M+]. HRMS calcd for C8H10NO2 152.0712, found 152.0698.

Aufarbeitung

  1. customwas removed by evaporation
  2. customthe product precipitated with diethyl ether
  3. customThe diethyl ether was removed by evaporation

Quellen und Nachweise

ORD-Eintrag
ord-1b2668063c35463880a13e4b955aea22
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08524657B2

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