2-(tert-butoxycarbonylamino)-N-(4-cyanophenyl)acetamide → 2-amino-N-(4-cyanophenyl)acetamide hydrochloride

HRID 964988Notes

Reaction equation

HRID 964988 reaction equation
[ClH:1].C(OCC)(=O)C.C(OC([NH:15][CH2:16][C:17]([NH:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]#[N:27])=[CH:22][CH:21]=1)=[O:18])=O)(C)(C)C>>[ClH:1].[NH2:15][CH2:16][C:17]([NH:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]#[N:27])=[CH:22][CH:21]=1)=[O:18]

Participants

3

Reactant 2

HCID 187889442-(tert-butoxycarbonylamino)-N-(4-cyanophenyl)acetamideHCID 21866389Hydrogen chloride-ethyl acetate

Product 1

HCID 187889452-amino-N-(4-cyanophenyl)acetamide hydrochloride

Procedure

45.5 ml of a solution of 4N-hydrogen chloride/ethyl acetate was added to 10 g of 2-(tert-butoxycarbonylamino)-N-(4-cyanophenyl)acetamide in a closed vessel and stirred for 18 hours. The crystals formed were removed by filtration, washed with ethyl acetate and then dried under a reduced pressure to obtain 7.7 g of 2-amino-N-(4-cyanophenyl)acetamide hydrochloride. 58.8 ml of an 5 aqueous saturated solution of sodium hydrogencarbonate and 20 ml of water were added to 3.7 g of the hydrochloride and stirred for 1 hour. The crystals thus formed were taken out by filtration and dried under a reduced pressure to obtain 2.5 g of 2-amino-N-(4-cyanophenyl)acetamide.

Workup

  1. customThe crystals formed
  2. customwere removed by filtration
  3. washwashed with ethyl acetate
  4. customdried under a reduced pressure

Sources & evidence

ORD record
ord-d26fa42500bf4a41a650ce2373b6f2b1
Source dataset
uspto-grants-1998_06
Patent number
US05773442

Reaction notes

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