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

HRID 2412420Notes

Reaction equation

HRID 2412420 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-c3a0ccdab36c423a80786e794c30e7a6
Source dataset
uspto-grants-1985_01
Patent number
US04492702

Reaction notes

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