Toluene → 2(1H)-Quinoxalinone

HRID 524368Notes

Reaction equation

HRID 524368 reaction equation
[C:1]1([NH2:8])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH2:7].[C:9](OCC)(=O)[CH:10]=[O:11].C1(C)C=CC=CC=1>C(O)C>[NH:7]1[C:2]2[C:1](=[CH:6][CH:5]=[CH:4][CH:3]=2)[N:8]=[CH:9][C:10]1=[O:11]

Participants

5

Reactant 3

HCID 1140TolueneHCID 7243O-PhenylenediamineHCID 70211Ethyl oxoacetate

Product 1

HCID 145262(1H)-QuinoxalinoneYield 93%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
45 °C

Procedure

To a stirred suspension of o-phenylenediamine (50 g, 462.9 mmol) in ethanol (200 mL), at rt was added a solution of ethyl glyoxalate in toluene (50%; 113 mL, 555.48 mmol) over a period of 45 min. After heating to 45° C. for 10 h, the mixture was left at rt under stirring. The precipitate was filtered and the residue was washed with water and dried to give 1H-quinoxalin-2-one as an off-white powder (63 g, 93%): 1H-NMR (300 MHz, d6-DMSO): δ=12.44 (1H, s), 8.19 (1H, s), 7.78 (1H, d), 7.55 (1H, dd), 7.32 (2H, m) ppm.

Workup

  1. waitthe mixture was left at rt
  2. filtrationThe precipitate was filtered
  3. washthe residue was washed with water
  4. customdried

Sources & evidence

ORD record
ord-c5efa7a6c98f49f8a965d7ea5b9c0a47
Source dataset
uspto-grants-2016_05
Patent number
US09340528B2

Reaction notes

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