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

HRID 2118736Notes

Reaction equation

HRID 2118736 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-5fd616fac1de47268a61f8d0edfeaa9a
Source dataset
uspto-grants-1987_07
Patent number
US04680298

Reaction notes

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