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

HRID 1994116Notes

Reaction equation

HRID 1994116 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>CCOC(C)=O.[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 82.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of N,N-dimethyl-2-[3-nitro-5-(trifluoromethyl)phenoxy]-ethanamine (490 mg, 1.61 mmol) and Pd/C (10 wt %, 49 mg) in EtOAc (15 mL) was stirred under an atmosphere of hydrogen until reaction complete was judged to be complete by LCMS. The mixture was filtered through Celite and rinsed with EtOAc. The filtrate was concentrated to yield the desired product as a brown solid (329 mg, 71%). LCMS: (FA) ES+ 275.2 (M+1).

Workup

  1. filtrationThe mixture was filtered through Celite
  2. washrinsed with EtOAc
  3. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-57d781bd7e914be0bf51f2125e2ab59e
Source dataset
uspto-grants-2010_01
Patent number
US07652041B2

Reaction notes

Loading…