Hydrochloric Acid → 4-(2-Amino-3,3-dimethylbutanoyl)benzonitrile hydrochloride

HRID 535778Notes

Reaction equation

HRID 535778 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9](=[O:23])[CH:10]([NH:15]C(=O)OC(C)(C)C)[C:11]([CH3:14])([CH3:13])[CH3:12])=[CH:5][CH:4]=1)#[N:2].[ClH:24]>CO>[ClH:24].[NH2:15][CH:10]([C:11]([CH3:14])([CH3:13])[CH3:12])[C:9]([C:6]1[CH:7]=[CH:8][C:3]([C:1]#[N:2])=[CH:4][CH:5]=1)=[O:23]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 68404944tert-Butyl 1-(4-cyanophenyl)-3,3-dimethyl-1-oxobutan-2-ylcarbamate

Product 1

HCID 682779744-(2-Amino-3,3-dimethylbutanoyl)benzonitrile hydrochlorideYield 93%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

tert-Butyl 1-(4-chlorophenyl)-3,3-dimethyl-1-oxobutan-2-ylcarbamate (Example 2a, 2.30 g, 7.06 mmol) and Zn(CN)2 (0.87 g, 7.4 mmol) were dissolved in DMF (20 mL) under N2 (g). Pd(PPh3)4 (0.86 g, 0.74 mmol) was added and the mixture was heated at 130° C. overnight. The mixture was cooled to rt, diluted with water and extracted with EtOAc. The organic phase was washed with brine, dried over Na2SO4 and evaporated. The product was purified on a silica column (EtOAc:hexane 1:10) to give tert-butyl 1-(4-cyanophenyl)-3,3-dimethyl-1-oxobutan-2-ylcarbamate (961 mg, 43%). tert-Butyl 1-(4-cyanophenyl)-3,3-dimethyl-1-oxobutan-2-ylcarbamate (961 mg, 3.04 mmol) was dissolved in 1.25 M HCl in MeOH at 0° C. and the mixture was stirred at rt for 8 h. The solvent was removed and the residue dried in vacuo to give 4-(2-amino-3,3-dimethyl-butanoyl)-benzonitrile hydrochloride (110 mg, 93%).

Workup

  1. customThe solvent was removed
  2. customthe residue dried in vacuo

Sources & evidence

ORD record
ord-a26bf46d8f2f4061a417f85c87858b11
Source dataset
uspto-grants-2014_10
Patent number
US08859556B2

Reaction notes

Loading…