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

HRID 1248948Notes

Reaction equation

HRID 1248948 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 is stirred and refluxed for two hours. The reaction mixture is poured on ice, extracted with ethyl acetate, the organic extracts are dried and concentrated to yield an oil. The crude residue is eluted on a silica gel column with ethylacetate-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 is poured on ice
  4. extractionextracted with ethyl acetate
  5. customthe organic extracts are dried
  6. concentrationconcentrated
  7. customto yield an oil
  8. washThe crude residue is eluted on a silica gel column with ethylacetate-hexane (1:2)
  9. customyielding the product of this example as a yellow solid, m.p. 72°-75° C.

Sources & evidence

ORD record
ord-b0c11db76a5c4b37a144dc17c92923c0
Source dataset
uspto-grants-1986_12
Patent number
US04628055

Reaction notes

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