Pyridine → Pyrazinecarboxylic acid, 4-methylphenyl ester

HRID 1088239Notes

Reaction equation

HRID 1088239 reaction equation
[N:1]1[CH:6]=[CH:5][N:4]=[CH:3][C:2]=1[C:7](Cl)=[O:8].N1C=CC=CC=1.[CH3:16][C:17]1[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=1>C(Cl)Cl>[N:1]1[CH:6]=[CH:5][N:4]=[CH:3][C:2]=1[C:7]([O:23][C:20]1[CH:21]=[CH:22][C:17]([CH3:16])=[CH:18][CH:19]=1)=[O:8]

Participants

5

Reactant 3

HCID 1049PyridineHCID 2879P-CresolHCID 88279Pyrazinecarbonyl chloride

Product 1

HCID 122713Pyrazinecarboxylic acid, 4-methylphenyl esterYield 28.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 3.5 g (25 mmol) of pyrazinoyl chloride dissolved in methylene chloride (20 mL) and pyridine (2 mL) cooled to 0° C. in a 50 mL round bottom flask was added 4-methyl-phenol (3.2 g, 30 mmol). Upon completion of the reaction and isolation as described above, recrystallization from hexanes yielded 1.51 g (24% yield) of the crystalline title compound; m.p.: 120°-123° C. Elemental Analysis: C12H10N2O2Calcd: C:67.28, H:4.71. Found: C:67.4, H:4.66.

Workup

  1. customUpon completion of the reaction and isolation
  2. customrecrystallization from hexanes

Sources & evidence

ORD record
ord-1537a98ca89947739e951c3d323e0664
Source dataset
uspto-grants-1990_10
Patent number
US04962111

Reaction notes

Loading…