Glyoxal → Quinoxaline, 6-nitro-

HRID 730272

Reaction equation

HRID 730272 reaction equation
N1C2C(=CC(N)=CC=2)N=[CH:3][CH:2]=1.[N+:12]([C:15]1[CH:20]=[CH:19][C:18]([NH2:21])=[C:17]([NH2:22])[CH:16]=1)([O-:14])=[O:13].C(C=O)=O>C(#N)C>[N+:12]([C:15]1[CH:16]=[C:17]2[C:18](=[CH:19][CH:20]=1)[N:21]=[CH:3][CH:2]=[N:22]2)([O-:14])=[O:13]

Participants

5

Reactant 3

HCID 7860GlyoxalHCID 2378596-QuinoxalinamineHCID 51117914-Nitro-1,2-phenylenediamine

Product 1

HCID 96029Quinoxaline, 6-nitro-

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Quinoxaline-6-ylamine. To a round-bottomed flask equipped with magnetic stirring was added 4-nitro-1,2-phenylenediamine (1.0 g, 6.5 mmol, Aldrich), acetonitrile (10 mL) and glyoxal (2.2 mL, 19 mmol, 40 wt. % in water, Aldrich). The reaction mixture was allowed to stir at 50° C. for 12 h, then concentrated in vacuo to yield 1.1 g crude 6-nitro-quinoxaline. The crude product was dissolved in methanol, treated with 10% Pd/C (10 mg, Aldrich) and stirred under H2 (1 atm) at 25° C. overnight. The reaction mixture was filtered through Celite and the filtrate was concentrated in vacuo to provide the title product. MS (ESI, pos. ion) m/z: 146 (M+1).

Workup

  1. customTo a round-bottomed flask equipped
  2. stirringto stir at 50° C. for 12 h
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b7881e4a193d4b18a16b0c58fc1c307b
Source dataset
uspto-grants-2009_09
Patent number
US07582657B2

Linked notes

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