Glyoxal → HCID 77231154, compound

HRID 2171000Notes

Reaction equation

HRID 2171000 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[C:4]([NH2:9])[C:3]=1[NH2:10].[CH:11]([CH:13]=O)=O>C1COCC1.O>[Cl:8][C:6]1[CH:7]=[C:2]([Cl:1])[C:3]2[C:4]([N:5]=1)=[N:9][CH:11]=[CH:13][N:10]=2

Participants

5

Reactant 2

HCID 7860GlyoxalHCID 223360774,6-Dichloropyridine-2,3-diamine

Product 1

HCID 77231154HCID 77231154, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4.81 g (27 mmol) 4,6-dichloro-pyridine-2,3-diamine (synthesis described in J. E. Schelling, C. A. Salemink, Rec. Tray. Chim. Pays-Bas 91, 650 [1972]) in 50 ml THF was treated with 5.22 g (27 mmol) of a 30% solution of glyoxal in water and the mixture was stirred for 3 days at room temperature. The reaction mixture was evaporated and the residue was partitioned between dichloromethane and diluted sodium carbonate solution. The organic phase was dried over sodium sulfate and evaporated. The residue was chromatographed on a silica gel column with cyclohexane/ethyl acetate as eluent yielding 6,8-dichloro-pyrido[2,3-b]pyrazine as off-white fine needles; HPLC/MS (B): 1.93 min, [M+H] 200.

Workup

  1. customThe reaction mixture was evaporated
  2. customthe residue was partitioned between dichloromethane and diluted sodium carbonate solution
  3. dry with materialThe organic phase was dried over sodium sulfate
  4. customevaporated
  5. customThe residue was chromatographed on a silica gel column with cyclohexane/ethyl acetate as eluent

Sources & evidence

ORD record
ord-e1e86b2fc4c84196b86151c3cb371551
Source dataset
uspto-grants-2015_06
Patent number
US09051318B2

Reaction notes

Loading…