Thionyl Chloride → 2-Amino-3-nitrobenzoyl chloride

Reaction equation

[NH2:1][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4](O)=[O:5].S(Cl)([Cl:16])=O>>[NH2:1][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([Cl:16])=[O:5]

Participants

Reactant 2

HCID 24386Thionyl Chloride

HCID 2196332-Amino-3-nitrobenzoic acid

Product 1

HCID 212519672-Amino-3-nitrobenzoyl chlorideYield 100%

Procedure

A mixture of 9.90 parts of 2-amino-3-nitrobenzoic acid and 32.4 parts of thionyl chloride was stirred for 15 min at reflux temperature under argon. The excess of thionyl chloride was evaporated, yielding 10.8 parts (100%) of 2-amino-3-nitrobenzoyl chloride (interm. 39).

Workup

temperatureat reflux temperature under argon
customThe excess of thionyl chloride was evaporated

Sources & evidence

ORD record: ord-2efa173836474511a5a4f86436526802
Source dataset: uspto-grants-1993_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05270464

Reaction notes

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