Aniline → Methyl 3-anilinopyrazine-2-carboxylate

HRID 2226847Notes

Reaction equation

HRID 2226847 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.CC1C=CC(S(O)(=O)=O)=CC=1.O>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 6115AnilineHCID 521998p-Toluenesulfonic acid monohydrateHCID 13318551Methyl 3-bromopyrazine-2-carboxylate

Product 1

HCID 13370930Methyl 3-anilinopyrazine-2-carboxylate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 9.5g. of methyl 2-bromo-3pyrazine carboxylate, 8.2g. of aniline, 0.5g. of ptoluene 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 9.5g
  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-a5566d8c26444af8804393dc8da54fd6
Source dataset
uspto-grants-1994_09
Patent number
US05350755

Reaction notes

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