Methanol → Methyl 3-aminobenzoate hydrochloride

HRID 647018Notes

Reaction equation

HRID 647018 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=[O:6].[CH3:11]O.S(Cl)([Cl:15])=O>C(OCC)C>[ClH:15].[CH3:11][O:6][C:5](=[O:7])[C:4]1[CH:8]=[CH:9][CH:10]=[C:2]([NH2:1])[CH:3]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 74193-Aminobenzoic AcidHCID 24386Thionyl Chloride

Product 1

HCID 12238913Methyl 3-aminobenzoate hydrochloride

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

The title compound is prepared according to the method of Example 9 using 13.7 g (0.1 mole) of m-aminobenzoic acid, 250 ml of methanol, and 21.9 ml (0.29 mole) of thionyl chloride, except that the mixture is not heated. After concentration of reduced pressure, the product is shaken with diethyl ether, producing 18.7 g (0.10 mole) of crystalline solid. Structure is confirmed by NMR spectrum.

Workup

  1. temperatureis not heated

Sources & evidence

ORD record
ord-68218c2c10c64407a9a7a0ea7e306f16
Source dataset
uspto-grants-1983_10
Patent number
US04407746

Reaction notes

Loading…