Nitric Acid → HCID 89923780, compound

HRID 1500905Notes

Reaction equation

HRID 1500905 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:15])[CH2:10][C:11]([F:14])([F:13])[F:12])=[C:4]([F:16])[CH:3]=1.[N+:17]([O-])([OH:19])=[O:18]>OS(O)(=O)=O>[Cl:1][C:2]1[CH:7]=[C:6]([N+:17]([O-:19])=[O:18])[C:5]([NH:8][C:9](=[O:15])[CH2:10][C:11]([F:13])([F:14])[F:12])=[C:4]([F:16])[CH:3]=1

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 89924300HCID 89924300, compound

Product 1

HCID 89923780HCID 89923780, compoundYield 17%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

A solution of N-(4-chloro-2-fluorophenyl)-3,3,3-trifluoropropanamide (2 g, 7.8 mmol) in 15 mL of concentrated H2SO4 was added 1 mL of concentrated nitric acid and stirred at room temperature overnight. The reaction was monitored by LC-MS. The reaction mixture was poured into 20 mL of ice-water. The mixture was filtered to give the solid crude N-(4-chloro-2-fluoro-6-nitrophenyl)-3,3,3-trifluoropropanamide (600 mg, yield: 17%) which was further purified by column chromatography (PE/EtOAc=6/1). MS obsd. (ESI+) [(M+H)+] 301.

Workup

  1. filtrationThe mixture was filtered

Sources & evidence

ORD record
ord-34da38e31ac14c5396f9ce3db71efd8b
Source dataset
uspto-grants-2015_12
Patent number
US09206191B2

Reaction notes

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