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

HRID 1004028Notes

Reaction equation

HRID 1004028 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-2ccdf3c4969e46af8927b645e9347c47
Source dataset
uspto-grants-2000_04
Patent number
US06048864

Reaction notes

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