Ethyl oxoacetate → HCID 86680400, compound

HRID 1023158Notes

Reaction equation

HRID 1023158 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:12]=[CH:13][C:14]=1[NH2:15])[O:5][CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8].[C:16](OCC)(=O)[CH:17]=[O:18]>C1(C)C=CC=CC=1>[O:18]=[C:17]1[CH:16]=[N:1][C:2]2[C:14](=[CH:13][CH:12]=[C:4]([O:5][CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH:3]=2)[NH:15]1

Participants

4

Reactant 2

HCID 70211Ethyl oxoacetateHCID 57763326HCID 57763326, compound

Product 1

HCID 86680400HCID 86680400, compoundYield 71.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of ethyl 2-(3,4-diaminophenoxy)acetate (1.3 g, 6.18 mmol) in toluene (10 mL) was added ethyl glyoxalate solution (2.52 mL, 12.37 mmol) and the reaction mixture was heated at 90° C. for 4 h. The reaction was cooled to room temperature. The solid was filtered, washed with diethyl ether (10 mL) and dried to yield ethyl 2-((2-oxo-1,2-dihydroquinoxalin-6-yl)oxy)acetate (1.1 g, 68%). LCMS: RT 1.18 min. LCMS (ES-API), m/z 247(−ve mode).

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. filtrationThe solid was filtered
  3. washwashed with diethyl ether (10 mL)
  4. customdried

Sources & evidence

ORD record
ord-fa82d5ac0f8141dc85782d2c264355ae
Source dataset
uspto-grants-2014_05
Patent number
US08722670B2

Reaction notes

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