O-Phenylenediamine → 3-Methylquinoxalin-2-ol

HRID 868961Notes

Reaction equation

HRID 868961 reaction equation
[C:1]1([NH2:8])[C:2]([NH2:7])=[CH:3][CH:4]=[CH:5][CH:6]=1.C([O:11][C:12](=O)[C:13](=O)[CH3:14])C>C(O)C>[CH3:14][C:13]1[C:12](=[O:11])[NH:7][C:2]2[C:1]([N:8]=1)=[CH:6][CH:5]=[CH:4][CH:3]=2

Participants

4

Reactant 2

HCID 7243O-PhenylenediamineHCID 12041Ethyl pyruvate

Product 1

HCID 263843-Methylquinoxalin-2-ol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of benzene-1,2-diamine (10.8 g, 100 mmol) in ethanol (500 mL) was treated with a solution of ethyl-2-oxopropanoate (11.22 g, 110 mmol) slowly at 0° C., and the resulting suspension was stirred at room temperature for 1 h, then filtered. An off-white solid was collected (15.85 g). MS (ESI): m/z 161 [M+H]+.

Workup

  1. filtrationfiltered
  2. customAn off-white solid was collected (15.85 g)

Sources & evidence

ORD record
ord-39fae0f9818b4499a28e049409c1dbcc
Source dataset
uspto-grants-2015_03
Patent number
US08969349B2

Reaction notes

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