Trifluoroacetic acid → N-Isopropyl-4-fluoro-2-nitroaniline

HRID 1734549Notes

Reaction equation

HRID 1734549 reaction equation
[F:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1.CO[C:14](OC)([CH3:16])[CH3:15].FC(F)(F)C(O)=O>C1(C)C=CC=CC=1.FC(F)(F)C(O)=O.N1C=CC=CC=1.CCOC(C)=O.CCCCCC>[F:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][CH:14]([CH3:16])[CH3:15])=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1

Participants

8

Reactant 3

HCID 6422Trifluoroacetic acidHCID 64952,2-Dimethoxypropane2×HCID 677694-Fluoro-2-nitroaniline2×

Product 1

HCID 2775219N-Isopropyl-4-fluoro-2-nitroanilineYield 58%

Reagents, catalysts & solvents 4

HCID 6422Trifluoroacetic acidCatalystHCID 1049PyridineSolvent2×HCID 1140TolueneSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

4-fluoro-2-nitroaniline (15.6 g; 0.1 mole), 2,2-dimethoxypropane (24.6 ml; 0.2 mole) and trifluoroacetic acid [TFA] (23.1 ml; 0.005 moles) were dissolved in toluene (500 ml) and stirred for 1 hr. BH3 * pyridine (10.0 ml; 0.1 moles) was added in 1.0 ml increments. The reaction was exothermic, and the reaction progress was monitored by tlc 40% EtOAc/Hexane. Additional TFA, BH3 * pyridine and 2,2-dimethoxypropane were added until the tlc indicated that the 4-fluoro-2-nitroaniline was consumed. The reaction mixture was placed on a bed of silica and eluted with 10% methyl-t-butylether/hexane. The product was the first major component to elute, which produced 11.2 g (58%) of a yellow oil.

Workup

  1. customwas consumed
  2. washeluted with 10% methyl-t-butylether/hexane
  3. washto elute

Sources & evidence

ORD record
ord-6f7e382324f24532a6266eb407150cf3
Source dataset
uspto-grants-1996_07
Patent number
US05534521

Reaction notes

Loading…