Sulfuryl chloride → Benzoic acid, 2-amino-5-chloro-4-methoxy-, methyl ester

HRID 1577344Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:13])[C:4]1[C:5](=[CH:7][C:8]([O:11][CH3:12])=[CH:9][CH:10]=1)[NH2:6].S(Cl)([Cl:17])(=O)=O>>[CH3:1][O:2][C:3](=[O:13])[C:4]1[C:5](=[CH:7][C:8]([O:11][CH3:12])=[C:9]([Cl:17])[CH:10]=1)[NH2:6]

Participants

Reactant 2

HCID 24648Sulfuryl chloride

HCID 12919999Methyl 2-amino-4-methoxybenzoate

Product 1

HCID 12920001Benzoic acid, 2-amino-5-chloro-4-methoxy-, methyl esterYield 90%

Procedure

Treatment of methyl-4-methoxyanthranilate with sulfuryl chloride as described above afforded methyl-4-methoxy-5-chloroanthranilate, M.P., 197°-200° C. in 90% yield.

Sources & evidence

ORD record: ord-98a1688efad540bd8b405bfb653c85e3
Source dataset: uspto-grants-1981_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04287341

Reaction notes

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