Hydrochloric Acid → 1-(2-aminophenyl)propan-1-one

HRID 1518911Notes

Reaction equation

HRID 1518911 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[C:4]#N.[CH2:10]([Mg]Br)[CH3:11].Cl.[O:15]1CCCC1>>[NH2:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[C:4](=[O:15])[CH2:10][CH3:11]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 729132-AminobenzonitrileHCID 178418443HCID 178418443, compound

Product 1

HCID 2946511-(2-aminophenyl)propan-1-oneYield 56%

Procedure

2-Aminobenzonitrile (1 mmol) was disposed in anhydrous tetrahydrofuran (5 ml) is followed by adding ethylmagnesium bromide (10 equivalent weights) at 0° C. under nitrogen gas atmosphere and reacting for 4 hours to obtain a reaction product. The pH of the reaction product was adjusted to be in the range of 3 to 4 using 1N HCl, followed by partitioning using ethyl acetate and saturated NaHCO3 for three times. The ethyl acetate layer was collected and purified using a silica gel column (n-hexane/acetone=4:1), thereby obtaining [1-(2-aminophenyl)propan-1-one] (83.5 mg, yield 56%).

Workup

  1. customto obtain a reaction product
  2. customby partitioning
  3. customThe ethyl acetate layer was collected
  4. custompurified

Sources & evidence

ORD record
ord-63862ca7d2524f288c6d072a393f8e62
Source dataset
uspto-grants-2015_07
Patent number
US09073833B1

Reaction notes

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