Formic Acid → Formanilide

HRID 916285Notes

Reaction equation

HRID 916285 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)([O-])=O.[CH:10](O)=[O:11]>[Pt].[O-2].[V+5].[O-2].[O-2].[O-2].[O-2].[V+5]>[CH:10]([NH:1][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)=[O:11]

Participants

5

Reactant 2

HCID 284Formic AcidHCID 7416Nitrobenzene

Product 1

HCID 7671FormanilideYield 79.9%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 178419084HCID 178419084, compoundCatalyst

Conditions

Temperature
92.5 °C

Procedure

Nitrobenzene (12.31 g, 100 mmol), formic acid (80%; 278 mL, 328.0 g), a sulfided platinum catalyst (5% Pt on charcoal, Engelhard No. 43045, lot No. 08554; dry weight 1.55 g) and vanadium(v) oxide (57 mg) were charged under argon in a double-walled 0.3 L stirring vessel with temperature control. The argon flow was stopped and the slurry was heated to 91-94° C. for 2 h. HPLC analysis of the reaction mixture indicated a 79.9% yield of formanilide, accompanied by 18.3% of aniline.

Sources & evidence

ORD record
ord-82e16fdb635f4d3e938bb502685d6335
Source dataset
uspto-grants-2007_09
Patent number
US07268255B2

Reaction notes

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