Ammonia → 4-[(3-Amino-2-hydroxypropyl)oxy]benzonitrile

HRID 2180008Notes

Reaction equation

HRID 2180008 reaction equation
CC(O)C.[O:5]1[CH2:7][CH:6]1[CH2:8][O:9][C:10]1[CH:17]=[CH:16][C:13]([C:14]#[N:15])=[CH:12][CH:11]=1.[NH3:18]>>[C:14]([C:13]1[CH:16]=[CH:17][C:10]([O:9][CH2:8][CH:6]([OH:5])[CH2:7][NH2:18])=[CH:11][CH:12]=1)#[N:15]

Participants

4

Reactant 3

HCID 222AmmoniaHCID 3776IsopropanolHCID 27643014-(2-Oxiranylmethoxy)benzenecarbonitrile

Product 1

HCID 167827394-[(3-Amino-2-hydroxypropyl)oxy]benzonitrileYield 46%

Procedure

IPA (300 mL) was added to a stirred suspension of 4-(2-oxiranylmethoxy)benzonitrile (from step (i) above; 100 g; 571 mmol) in NH3 (500 mL; conc.), and the reaction mixture was stirred at rt for 3 days. The precipitate was filtered off and the residue concentrated and recrystallized from MeCN to give the sub-title compound in a 46% yield.

Workup

  1. filtrationThe precipitate was filtered off
  2. concentrationthe residue concentrated
  3. customrecrystallized from MeCN

Sources & evidence

ORD record
ord-aa06d0c4142e4ebeb219d27ae209acb1
Source dataset
uspto-grants-2005_05
Patent number
US06887881B1

Reaction notes

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