Aniline → HCID 18626180, compound

HRID 1859660Notes

Reaction equation

C(Cl)(=O)C(Cl)=O.[N+:7]([C:10]1[CH:11]=[C:12]([CH:16]=[CH:17][C:18]=1[CH2:19][CH3:20])[C:13]([OH:15])=O)([O-:9])=[O:8].CN(C=O)C.[NH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>>[N+:7]([C:10]1[CH:11]=[C:12]([CH:16]=[CH:17][C:18]=1[CH2:19][CH3:20])[C:13]([NH:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:15])([O-:9])=[O:8]

Participants

Reactant 4

HCID 6115Aniline

HCID 6228Dimethylformamide

HCID 65578Oxalyl chloride

HCID 81670864-Ethyl-3-nitrobenzoic acid

Product 1

HCID 18626180HCID 18626180, compoundYield 74%

Procedure

Prepared according to the procedure described for Example 1 using oxalyl chloride (2.0 mL, 22.93 mmol), 3-nitro-4-ethylbenzoic acid (4.00 g, 20.51 mmol), DMF (1.0 mL, 12.92 mmol), and aniline (3.8 mL, 41.70 mmol) to afford the 5 product (4.1 g); m.p. 111-113° C. after trituration in hexane.

Workup

customPrepared

Sources & evidence

ORD record: ord-6c88ead14ee943bea76f30fc886d0076
Source dataset: uspto-grants-2003_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06528528B2

Reaction notes

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