N-(4-cyano-2-methyl-3-(trifluoromethyl)phenyl)pivalamide → 4-Amino-3-methyl-2-(trifluoromethyl)benzonitrile

HRID 501554Notes

Reaction equation

HRID 501554 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([NH:9]C(=O)C(C)(C)C)=[C:5]([CH3:16])[C:4]=1[C:17]([F:20])([F:19])[F:18])#[N:2]>Cl.CCO>[NH2:9][C:6]1[CH:7]=[CH:8][C:3]([C:1]#[N:2])=[C:4]([C:17]([F:18])([F:19])[F:20])[C:5]=1[CH3:16]

Participants

3

Reactant 1

HCID 21875020N-(4-cyano-2-methyl-3-(trifluoromethyl)phenyl)pivalamide

Product 1

HCID 218752104-Amino-3-methyl-2-(trifluoromethyl)benzonitrileYield 87.1%

Reagents, catalysts & solvents 1

HCID 21887872Ethanol hydrochlorideSolvent

Procedure

A solution of the mixed product from 18C (7.53 g, 26.5 mmol) in 120 mL of concentrated HCl/EtOH (1:1) was refluxed for 14 h. After cooling to rt, the solution was concentrated under reduced pressure. The resulting residue was dissolved in EtOAc, washed with saturated aqueous NaHCO3 (2×) and brine (1×), dried (MgSO4), filtered and concentrated. The residue was chromatographed (silica gel), eluting with chloroform/MeOH (98:2) to furnish the title compound (4.62 g, 87%). MS (ES) m/z 201 [M+1]+.

Workup

  1. concentrationthe solution was concentrated under reduced pressure
  2. dissolutionThe resulting residue was dissolved in EtOAc
  3. washwashed with saturated aqueous NaHCO3 (2×) and brine (1×)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was chromatographed (silica gel)
  8. washeluting with chloroform/MeOH (98:2)

Sources & evidence

ORD record
ord-2e0b1f21f91b445c892b1e48c1cb7594
Source dataset
uspto-grants-2010_08
Patent number
US07772267B2

Reaction notes

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