Benzil → 6-methyl-2,3-diphenylquinoxaline

HRID 2083849Notes

Reaction equation

HRID 2083849 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[NH2:9].[C:10]1([C:16]([C:18]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=O)=O)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>C(O)(=O)C>[CH3:8][C:5]1[CH:4]=[C:3]2[C:2](=[CH:7][CH:6]=1)[N:1]=[C:18]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:16]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[N:9]2

Participants

4

Reactant 2

HCID 8651BenzilHCID 103323,4-Diaminotoluene

Product 1

HCID 15520156-methyl-2,3-diphenylquinoxaline

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

1,2-Diamino-4-methylbenzene (25.0 g, 0.20 mol) and benzil (43 g, 0.20 mol) were refluxed in ethanoic acid (250 ml) overnight. The solvent was evaporated in vacua and the black residue recrystallised three times from ethanol to give pale brown crystals of 6-methyl-2,3-diphenylquinoxaline, 39.6 g, 65% (m.pt. 114.5-116° C. (lit.i 115-116° C.)). 1H NMR (CDCl3, 300 MHz) δ 8.08 (d, J 8.4 Hz, 1H, Hs of quinoxaline), 7.97 (bs, 1H, Hs of quinoxaline), 7.60 (d of d, J 8.4 Hz, J 1.8 Hz, 1H, Hs of quinoxaline), 7.50-7.58 (m, 4H, phenyl rings), 7.30-7.38 (m, 6H, phenyl rings), 2.62 (s, 3H, CH3).

Workup

  1. customThe solvent was evaporated in vacua
  2. customthe black residue recrystallised three times from ethanol

Sources & evidence

ORD record
ord-06bfcef7558e4389b6310db109e37cb3
Source dataset
uspto-grants-2004_04
Patent number
US06716371B1

Reaction notes

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