Hydrochloric Acid → 4-Amino-3-methyl-2-(trifluoromethyl)benzonitrile

HRID 913558Notes

Reaction equation

HRID 913558 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.[OH-].[Na+].CCOC(C)=O>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

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 21875020N-(4-cyano-2-methyl-3-(trifluoromethyl)phenyl)pivalamide

Product 1

HCID 218752104-Amino-3-methyl-2-(trifluoromethyl)benzonitrile

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

The crude N-[4-cyano-2-methyl-3-(trifluoromethyl)phenyl]-2,2-dimethylpropanamide from Example 191B was dissolved in EtOH (5 mL) and conc. HCl (5 mL). The resulting mixture was heated to 70° C. for 20 min. The cooled reaction's pH was adjusted to ca. 8 with 6 N NaOH. EtOAc (20 mL) was added and the isolated organic portion was dried (Na2SO4), filtered, and concentrated to afford the title compound: MS (ES) m/z 201 (M+1).

Workup

  1. dry with materialthe isolated organic portion was dried (Na2SO4)
  2. filtrationfiltered
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-ce1ad950012b47a6afc176d648b532bc
Source dataset
uspto-grants-2011_09
Patent number
US08026262B2

Reaction notes

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