Hydrochloric Acid → 5-(4-Amino-2-methyl-3-oxobutan-2-yl)-2-fluorobenzonitrile hydrochloride

HRID 83883Notes

Reaction equation

HRID 83883 reaction equation
[N:1]([CH2:4][C:5](=[O:18])[C:6]([C:9]1[CH:10]=[CH:11][C:12]([F:17])=[C:13]([CH:16]=1)[C:14]#[N:15])([CH3:8])[CH3:7])=[N+]=[N-].[ClH:19]>CCO.O=[Pt]=O>[ClH:19].[NH2:1][CH2:4][C:5](=[O:18])[C:6]([C:9]1[CH:10]=[CH:11][C:12]([F:17])=[C:13]([CH:16]=1)[C:14]#[N:15])([CH3:8])[CH3:7]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 86662254HCID 86662254, compound

Product 1

HCID 667404015-(4-Amino-2-methyl-3-oxobutan-2-yl)-2-fluorobenzonitrile hydrochlorideYield 65%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 702EthanolSolvent

Procedure

To a stirred solution of 5-(4-azido-2-methyl-3-oxobutan-2-yl)-2-fluorobenzonitrile (6.1 g, 24.7 mmol) in EtOH (100 mL) was added conc HCl (20 mL) and PtO2 (112 mg, 0.49 mmol, 0.02 eq). The mixture was stirred at 1 atm of H2 gas for 12 h, filtered through Celite™ and evaportated in vacuo. The residue was partitioned in DCM and water, and the aqueous layer was evaporated in vacuo. The resulting residue was triturated with Et2O-Hex to give 5-(4-amino-2-methyl-3-oxobutan-2-yl)-2-fluorobenzonitrile hydrochloride as a yellow solid (6 g, 65%). 1H NMR (400 MHz, CD3OD) δ 7.74-7.68 (m, 2H), 7.37 (t, J=8.8 Hz, 1H), 3.89 (s, 2H), 1.58 (s, 6H).

Workup

  1. filtrationfiltered through Celite™
  2. customThe residue was partitioned in DCM
  3. customwater, and the aqueous layer was evaporated in vacuo
  4. customThe resulting residue was triturated with Et2O-Hex

Sources & evidence

ORD record
ord-2afbe25289fd46bd86ff1c7d261210c6
Source dataset
uspto-grants-2014_09
Patent number
US08846739B2

Reaction notes

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