Methanol → Methyl 3-aminobenzoate hydrochloride

HRID 37775

Reaction equation

HRID 37775 reaction equation
[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]

Participants

4

Reactant 3

HCID 887MethanolHCID 74193-Aminobenzoic AcidHCID 24386Thionyl Chloride

Product 1

HCID 12238913Methyl 3-aminobenzoate hydrochlorideYield 98%

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-1b2668063c35463880a13e4b955aea22
Source dataset
uspto-grants-2013_09
Patent number
US08524657B2

Linked notes

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