Trifluoroacetic acid → N-isopropyl-4-methoxy-2-nitroaniline

HRID 1734550Notes

Reaction equation

HRID 1734550 reaction equation
[CH3:1][O:2][C:3]1[CH:9]=[CH:8][C:6]([NH2:7])=[C:5]([N+:10]([O-:12])=[O:11])[CH:4]=1.CO[C:15](OC)([CH3:17])[CH3:16].FC(F)(F)C(O)=O.FC1C=CC(N)=C([N+]([O-])=O)C=1>C1(C)C=CC=CC=1.FC(F)(F)C(O)=O.N1C=CC=CC=1.CCOC(C)=O.CCCCCC>[CH:15]([NH:7][C:6]1[CH:8]=[CH:9][C:3]([O:2][CH3:1])=[CH:4][C:5]=1[N+:10]([O-:12])=[O:11])([CH3:17])[CH3:16]

Participants

9

Reactant 4

HCID 6422Trifluoroacetic acidHCID 64952,2-Dimethoxypropane2×HCID 667934-Methoxy-2-nitroanilineHCID 677694-Fluoro-2-nitroaniline

Product 1

HCID 10750935N-isopropyl-4-methoxy-2-nitroanilineYield 62.8%

Reagents, catalysts & solvents 4

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

Procedure

4-methoxy-2-nitroaniline (16.8 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 13.2 g (62%) of a yellow solid.

Workup

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

Sources & evidence

ORD record
ord-a8f63cb830ea43e6842a5986a8a4bdf6
Source dataset
uspto-grants-1996_07
Patent number
US05534521

Reaction notes

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