N,N-dimethyl-2-(3-nitro-5-(trifluoromethyl)phenoxy)ethanamine → 3-[2-(Dimethylamino)ethoxy]-5-(trifluoromethyl)aniline

HRID 1050196Notes

Reaction equation

HRID 1050196 reaction equation
[CH3:1][N:2]([CH3:19])[CH2:3][CH2:4][O:5][C:6]1[CH:11]=[C:10]([C:12]([F:15])([F:14])[F:13])[CH:9]=[C:8]([N+:16]([O-])=O)[CH:7]=1>CO.[Pd]>[CH3:1][N:2]([CH3:19])[CH2:3][CH2:4][O:5][C:6]1[CH:7]=[C:8]([CH:9]=[C:10]([C:12]([F:13])([F:14])[F:15])[CH:11]=1)[NH2:16]

Participants

4

Reactant 1

HCID 66806497N,N-dimethyl-2-(3-nitro-5-(trifluoromethyl)phenoxy)ethanamine

Product 1

HCID 210495493-[2-(Dimethylamino)ethoxy]-5-(trifluoromethyl)anilineYield 90%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×

Procedure

A suspension of N,N-dimethyl-2-(3-nitro-5-(trifluoromethyl)phenoxy)ethanamine (75 mg, 0.270 mmol) in MeOH (5 mL) was added to a solution of Pd/C (57.4 mg, 0.539 mmol) in MeOH (5 mL). The mixture was hydrogenated at 26° C. for 3 h under a H2 atmosphere. Then the solution was filtered and concentrated to afford 3-(2-(dimethylamino)ethoxy)-5-(trifluoromethyl)aniline (60.3 mg, 0.243 mmol, 90% yield). TLC (PE/EA=1:1, Rf=0.5): 1H NMR (400 MHz, CD3OD) δ 6.56 (s, 1H), 6.48 (s, 2H), 4.24-4.17 (m, 2H), 3.18 (t, J=5.1 Hz, 2H), 2.67 (s, 6H). ES-LCMS m/z 249 (M+H).

Workup

  1. filtrationThen the solution was filtered
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-a10951e094ca4bd6b0caceeac29969f8
Source dataset
uspto-grants-2016_07
Patent number
US09382238B2

Reaction notes

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