3,4-Diaminobenzonitrile → 2-Hydroxyquinoxaline-6-carbonitrile

HRID 72124

Reaction equation

HRID 72124 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[NH2:10])[C:5]#[N:6].O.[C:12](O)(=O)[CH:13]=[O:14]>Cl>[O:14]=[C:13]1[CH:12]=[N:1][C:2]2[C:9](=[CH:8][CH:7]=[C:4]([C:5]#[N:6])[CH:3]=2)[NH:10]1

Participants

4

Reactant 2

HCID 7372853,4-DiaminobenzonitrileHCID 15620607Glyoxylic acid, monohydrate

Product 1

HCID 451217302-Hydroxyquinoxaline-6-carbonitrile

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

To a stirred solution of 3,4-diaminobenzonitrile (5.00 g, 37.6 mmol) in 5% aq HCl (20 mL) was added glyoxilic acid monohydrate (4.32 g, 46.9 mmol). The mixture was stirred overnight at rt and filtered. The filter cake was washed with water and MeOH to afford 2-oxo-1,2-dihydroquinoxaline-6-carbonitrile as a grey solid which was used directly in the next step.

Workup

  1. filtrationfiltered
  2. washThe filter cake was washed with water and MeOH

Sources & evidence

ORD record
ord-f4d6d8765b134ec98904a66135422cd8
Source dataset
uspto-grants-2014_09
Patent number
US08828985B2

Linked notes

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