5-Methoxy-2-nitrobenzotrifluoride → 4-Methoxy-2-(trifluoromethyl)aniline

HRID 2308242Notes

Reaction equation

HRID 2308242 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][C:5]=1[C:12]([F:15])([F:14])[F:13])([O-])=O>C(OCC)(=O)C.[Pd]>[NH2:1][C:4]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][C:5]=1[C:12]([F:13])([F:14])[F:15]

Participants

4

Reactant 1

HCID 5485175-Methoxy-2-nitrobenzotrifluoride

Product 1

HCID 226017214-Methoxy-2-(trifluoromethyl)anilineYield 97%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 4-nitro-3-trifluoromethylanisole (26 g, 120 mmol) in ethyl acetate (250 mL) was hydrogenated over 10% palladium on carbon (5.3 g) at 50 psi for 1.5 h. At this time, the solution was filtered through Celite and washed with ethyl acetate (250 mL). The filtrate was concentrated in vacuo to give the title compound (22 g, 97%) as an amber oil which was pure enough for further use.

Workup

  1. filtrationAt this time, the solution was filtered through Celite
  2. washwashed with ethyl acetate (250 mL)
  3. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-11e8e202694b496998ba67271f1e2900
Source dataset
uspto-grants-2004_12
Patent number
US06835745B2

Reaction notes

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