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

HRID 1906414Notes

Reaction equation

HRID 1906414 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>[C:13]1([NH:12][C:2]2[C:7]([C:8]([O:10][CH3:11])=[O:9])=[N:6][CH:5]=[CH:4][N:3]=2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

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-c86684fef6434efe9908ed4cc8e1f61e
Source dataset
uspto-grants-1987_03
Patent number
US04652564

Reaction notes

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