O-Phenylenediamine → methyl 2-(3-oxo-4H-quinoxalin-2-yl)acetate

HRID 1733459Notes

Reaction equation

HRID 1733459 reaction equation
[C:1]([C:7]([O:9][CH3:10])=[O:8])#[C:2][C:3](OC)=[O:4].[C:11]1([NH2:18])[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[NH2:17]>CO>[O:4]=[C:3]1[NH:18][C:11]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[N:17]=[C:2]1[CH2:1][C:7]([O:9][CH3:10])=[O:8]

Participants

4

Reactant 2

HCID 7243O-PhenylenediamineHCID 12980Dimethyl acetylenedicarboxylate

Product 1

HCID 310826methyl 2-(3-oxo-4H-quinoxalin-2-yl)acetate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Dimethyl acetylenedicarboxylate (31.2 g., 0.22 mol.) was added slowly to a solution of o-phenylenediamine (21.6 g., 0.2 mol.) in methanol (400 ml.). The reaction mixture was stirred at room temperature for three hours and then cooled in an ice bath. The yellow solid was collected and washed with cold methanol. The solid was recrystallized from tetrahydrofuran (27.7 g., m.p. 230°-232° dec.).

Workup

  1. temperaturecooled in an ice bath
  2. customThe yellow solid was collected
  3. washwashed with cold methanol
  4. customThe solid was recrystallized from tetrahydrofuran (27.7 g., m.p. 230°-232° dec.)

Sources & evidence

ORD record
ord-056b27fad2be4a4daaca008259478062
Source dataset
uspto-grants-1980_12
Patent number
US04242342

Reaction notes

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