Ethanol → 3-(Hydroxyamino)-3,4-dihydroisoquinolin-1-amine

HRID 1174485Notes

Reaction equation

HRID 1174485 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:9][C:10]#[N:11])#[N:2].[NH2:12][OH:13].CCO>>[NH2:11][C:10]1[CH2:9][C:4]2[C:3](=[CH:8][CH:7]=[CH:6][CH:5]=2)[C:1](=[N:12][OH:13])[N:2]=1.[OH:13][NH:12][CH:10]1[CH2:9][C:4]2[C:3](=[CH:8][CH:7]=[CH:6][CH:5]=2)[C:1]([NH2:2])=[N:11]1

Participants

5

Reactant 3

HCID 702EthanolHCID 787HydroxylamineHCID 773682-Cyanobenzeneacetonitrile

Product 2

HCID 576727573-(Hydroxyamino)-3,4-dihydroisoquinolin-1-amineYield 185.4%HCID 765891383-aminoisoquinolin-1(4H)-one oxime

Procedure

A solution of 2-cyanophenylacetonitrile (1 g, 7 mmol) and hydroxylamine (1.7 cm3, 28.1 mmol, 4 eq) in EtOH (25 cm3) were stirred under reflux for 60 hours, after which the volatiles were removed under reduced pressure. The residue was recrystallised from EtOH-water (1:4, 15 cm3) to give the cyclised product 3-aminoisoquinolin-1(4H)-one oxime or 3-(hydroxyamino)-3,4-dihydroisoquinolin-1-amine (1.15 g, 85.9%) as a solid, mp 9.25-94.5° C.

Workup

  1. temperatureunder reflux for 60 hours
  2. customafter which the volatiles were removed under reduced pressure
  3. customThe residue was recrystallised from EtOH-water (1:4, 15 cm3)

Sources & evidence

ORD record
ord-8799f193856749c6bf5658a53eccbc39
Source dataset
uspto-grants-2010_11
Patent number
US07838483B2

Reaction notes

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