Magnesium → 3-Amino-4-cyano-5-(2,2,2-trifluoroethoxy)anisole

HRID 2228516Notes

Reaction equation

HRID 2228516 reaction equation
[N:1]([C:4]1[CH:5]=[C:6]([O:18][CH3:19])[CH:7]=[C:8]([O:12][CH2:13][C:14]([F:17])([F:16])[F:15])[C:9]=1[C:10]#[N:11])=[N+]=[N-].[Mg]>CO>[NH2:1][C:4]1[CH:5]=[C:6]([O:18][CH3:19])[CH:7]=[C:8]([O:12][CH2:13][C:14]([F:16])([F:17])[F:15])[C:9]=1[C:10]#[N:11]

Participants

4

Reactant 2

HCID 5462224MagnesiumHCID 184706173-Azido-4-cyano-5-(2,2,2-trifluoroethoxy)anisole

Product 1

HCID 184706143-Amino-4-cyano-5-(2,2,2-trifluoroethoxy)anisoleYield 88.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3-Azido-4-cyano-5-(2,2,2-trifluoroethoxy)anisole (5.66 g, 0.0208 mol) was added to a suspension of magnesium turnings (1.86 g, 0.0775 mol) in methanol (150 ml) and the reaction stirred at room temperature for 40 hours. The reaction was concentrated under reduced pressure to a minimum volume and ethyl acetate (200 ml) added. The mixture was washed with saturated aqueous ammonium chloride solution (75 ml) and brine (75 ml) and then dried (MgSO4), filtered and evaporated under reduced pressure. Trituration with diethyl ether:hexane gave the subtitle compound as a brown solid (4.51 g, 88%). Rf 0.46 (ethyl acetate:hexane, 1:1, v/v). MS m/z 247 (MH)+.

Workup

  1. concentrationThe reaction was concentrated under reduced pressure to a minimum volume and ethyl acetate (200 ml)
  2. additionadded
  3. washThe mixture was washed with saturated aqueous ammonium chloride solution (75 ml) and brine (75 ml)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-0f315aeb49d3433f9aa8d40a2f2f2f54
Source dataset
uspto-grants-2002_07
Patent number
US06417194B1

Reaction notes

Loading…