Toluene → Pyrido[2,3-b]pyrazin-2(1H)-one

HRID 385514Notes

Reaction equation

HRID 385514 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([NH2:7])[C:2]=1[NH2:8].C1(C)C=CC=CC=1.[O:16]=[CH:17][C:18](OCC)=O.C(OCC)C>O1CCOCC1>[NH:7]1[C:17](=[O:16])[CH:18]=[N:8][C:2]2[N:1]=[CH:6][CH:5]=[CH:4][C:3]1=2

Participants

6

Reactant 4

HCID 1140TolueneHCID 3283Diethyl EtherHCID 99562,3-DiaminopyridineHCID 70211Ethyl oxoacetate

Product 1

HCID 21780787Pyrido[2,3-b]pyrazin-2(1H)-one

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a suspension of 3.8 g of pyridine-2,3-diamine in 100 mL of dioxane, 7.1 g of a 45 to 50% toluene solution of ethyl oxoacetate was added, and the mixture was stirred at room temperature for 1 hour, and then heated under reflux while stirring for 1 hour. The reaction mixture was cooled with ice bath, and diethyl ether was added thereto. The solid was filtered off to obtain 3.9 g of pyrido(2,3-b)pyrazin-2(1H)-one as a light brown solid.

Workup

  1. additionwas added
  2. temperatureheated
  3. temperatureunder reflux
  4. stirringwhile stirring for 1 hour
  5. temperatureThe reaction mixture was cooled with ice bath
  6. filtrationThe solid was filtered off

Sources & evidence

ORD record
ord-dc2caacea5fa42ba80646c82ef51982f
Source dataset
uspto-grants-2013_02
Patent number
US08367831B2

Reaction notes

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