Sodium Bicarbonate → 2-amino-N-(4-cyanophenyl)acetamide

HRID 1106490Notes

Reaction equation

HRID 1106490 reaction equation
C(=O)([O-])O.[Na+].Cl.[NH2:7][CH2:8][C:9]([NH:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]#[N:19])=[CH:14][CH:13]=1)=[O:10]>O>[NH2:7][CH2:8][C:9]([NH:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]#[N:19])=[CH:14][CH:13]=1)=[O:10]

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 187889452-amino-N-(4-cyanophenyl)acetamide hydrochloride

Product 1

HCID 187889462-amino-N-(4-cyanophenyl)acetamideYield 81.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

An ethyl acetate solution (45.5 ml) of 4N hydrogen chloride solution was added to 10 g of 2-(tert-butoxycarbonylamino)-N-(4-cyanophenyl)acetamide in a closed vessel and the mixture was stirred for 18 hours. The crystals formed were collected by filtration, washed with ethyl acetate and then dried under a reduced pressure to give 7.7 g of 2-amino-N-(4-cyanophenyl)acetamide hydrochloride. Then, 58.8 ml of an aqueous saturated sodium hydrogencarbonate solution and 20 ml of water were added to 3.7 g of the hydrochloride thus obtained, and the mixture was stirred for 1 hour. The crystals thus formed were collected by filtration and dried under a reduced pressure to give 2.5 g of 2-amino-N-(4-cyanophenyl)acetamide.

Workup

  1. customthus obtained
  2. customThe crystals thus formed
  3. filtrationwere collected by filtration
  4. customdried under a reduced pressure

Sources & evidence

ORD record
ord-9abd78e9da01405e9341cddbb823ed7c
Source dataset
uspto-grants-2000_05
Patent number
US06057324

Reaction notes

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