4-Chloroaniline → HCID 13318566, compound

HRID 1156725Notes

Reaction equation

HRID 1156725 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:10](Br)=[N:9][CH:8]=[CH:7][N:6]=1)=[O:4].[Cl:12][C:13]1[CH:19]=[CH:18][C:16]([NH2:17])=[CH:15][CH:14]=1>C(OCC)(=O)C>[CH3:1][O:2][C:3]([C:5]1[C:10]([NH:17][C:16]2[CH:18]=[CH:19][C:13]([Cl:12])=[CH:14][CH:15]=2)=[N:9][CH:8]=[CH:7][N:6]=1)=[O:4]

Participants

4

Reactant 2

HCID 78124-ChloroanilineHCID 13318551Methyl 3-bromopyrazine-2-carboxylate

Product 1

HCID 13318566HCID 13318566, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 21.7 g 3-bromo-pyrazine-2-carboxylic acid methyl ester and 25.5 g 4-chloroaniline in 150 ml ethyl acetate is boiled 4 days at reflux. The solution is washed with 4 N hydrochloric acid, water and then with 2 N sodium carbonate. The organic phase is dried over sodium sulphate and evaporated to give the heading compound (recrystallised from isopropanol) m.p. 135°-136°.

Workup

  1. temperatureat reflux
  2. washThe solution is washed with 4 N hydrochloric acid, water
  3. dry with materialThe organic phase is dried over sodium sulphate
  4. customevaporated
  5. customto give
  6. customthe heading compound (recrystallised from isopropanol) m.p. 135°-136°

Sources & evidence

ORD record
ord-22b57c85d076457ab472d62ee6371399
Source dataset
uspto-grants-1982_06
Patent number
US04337198

Reaction notes

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