p-Toluenesulfonic acid → Methyl 3-anilinopyrazine-2-carboxylate

HRID 649564Notes

Reaction equation

HRID 649564 reaction equation
Br[C:2]1[C:7]([C:8]([O:10][CH3:11])=[O:9])=[N:6][CH:5]=[CH:4][N:3]=1.[NH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>O>[CH3:11][O:10][C:8]([C:7]1[C:2]([NH:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[N:3][CH:4]=[CH:5][N:6]=1)=[O:9]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 6115AnilineHCID 13318551Methyl 3-bromopyrazine-2-carboxylate

Product 1

HCID 13370930Methyl 3-anilinopyrazine-2-carboxylate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 9.5 g. of methyl 2-bromo-3-pyrazine carboxylate, 8.2 g. of aniline, 0.5 g. of p-toluene sulfonic acid and 100 ml. of water was stirred and refluxed for two hours. The reaction mixture was poured on ice, extracted with ethyl acetate, the organic extracts were dried and concentrated to yield an oil. The crude residue was eluted on a silica gel column with ethyl acetate-hexane (1:2) yielding the product of this example as a yellow solid, m.p. 72°-75° C.

Workup

  1. additionA mixture of 9.5 g
  2. temperaturerefluxed for two hours
  3. additionThe reaction mixture was poured on ice
  4. extractionextracted with ethyl acetate
  5. customthe organic extracts were dried
  6. concentrationconcentrated
  7. customto yield an oil
  8. washThe crude residue was eluted on a silica gel column with ethyl acetate-hexane (1:2)
  9. customyielding the product of this example as a yellow solid, m.p. 72°-75° C.

Sources & evidence

ORD record
ord-a60ca00dbb9c439b83be9637271294a0
Source dataset
uspto-grants-1988_04
Patent number
US04740511

Reaction notes

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