Methanol → methyl 4-Amino-3-methylsulfonylbenzoate

HRID 1534843Notes

Reaction equation

[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[S:11]([CH3:14])(=[O:13])=[O:12].S(Cl)(Cl)=O.[CH3:19]O>>[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([O:8][CH3:19])=[O:7])=[CH:4][C:3]=1[S:11]([CH3:14])(=[O:13])=[O:12]

Participants

Reactant 3

HCID 887Methanol

HCID 24386Thionyl Chloride

HCID 190960744-Amino-3-methanesulfonylbenzoic acid

Product 1

HCID 22041468methyl 4-Amino-3-methylsulfonylbenzoate

Procedure

Precursors of Example 28 starting from 4-chloro-3-methylsulfonylbenzoic acid via 4-N-hydrazino-3-methylsulfonylbenzoic acid (m.p. 243°-245° C.) and its hydrogenolytic N-N cleavage with Raney nickel catalyst in methanol/aq. NH3 under normal pressure at room temperature to give 4-amino-3-methylsulfonylbenzoic acid (m.p. 258°-262° C.) and subsequent reaction with thionyl chloride and methanol to give methyl 4-amino-3-methylsulfonylbenzoate (m.p. 146° C.).

Sources & evidence

ORD record: ord-fd06a696134f4f858add862390c664a6
Source dataset: uspto-grants-1992_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05091394

Reaction notes

Loading…