Methanol → Methyl 3-aminobenzoate hydrochloride

HRID 1664114Notes

Reaction equation

HRID 1664114 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, 3H, OCH3). Mass Spectrum (CI) 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-162ac83421ed456ab485b6b7d3a1670e
Source dataset
uspto-grants-2011_10
Patent number
US08039430B2

Reaction notes

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