Trifluoroacetic acid → 3-Amino-4-chloro-5-(4-hydroxybutan-2-yl)benzonitrile

HRID 921852Notes

Reaction equation

HRID 921852 reaction equation
[Cl:1][C:2]1[C:7]([CH:8]([CH2:10][CH2:11][OH:12])[CH3:9])=[CH:6][C:5]([C:13]#[N:14])=[CH:4][C:3]=1[NH:15]C(=O)OC(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:15][C:3]1[CH:4]=[C:5]([CH:6]=[C:7]([CH:8]([CH2:10][CH2:11][OH:12])[CH3:9])[C:2]=1[Cl:1])[C:13]#[N:14]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 131734941Tert-butyl (2-chloro-5-cyano-3-(4-hydroxybutan-2-yl)phenyl)carbamate

Product 1

HCID 899224133-Amino-4-chloro-5-(4-hydroxybutan-2-yl)benzonitrileYield 127.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Tert-butyl (2-chloro-5-cyano-3-(4-hydroxybutan-2-yl)phenyl)carbamate (184 mg, 0.566 mmol) was taken up in DCM (6 mL) and TFA (1.746 mL, 22.66 mmol) was added. The reaction was stirred at room temperature for 1 h. LCMS indicates a mixture of the alcohol and the TFA ester. The solvent was removed in vacuo and the material dissolved in 2N NH3 in MeOH. The solution was stirred at room temperature for 10 min and the solvent removed in vacuo. 3-amino-4-chloro-5-(4-hydroxybutan-2-yl)benzonitrile (162 mg) was obtained. The crude material was taken forward without purification.

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionthe material dissolved in 2N NH3 in MeOH
  3. stirringThe solution was stirred at room temperature for 10 min
  4. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-69bc3f9d5939457d81890c815bc5dce1
Source dataset
uspto-grants-2016_03
Patent number
US09273057B2

Reaction notes

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