Hydrochloric Acid → 6-Chloro-5-ethylamino-3-methoxypyrazine-2-carboxylic acid

HRID 441499Notes

Reaction equation

HRID 441499 reaction equation
[OH-].[Na+].[Cl:3][C:4]1[N:9]=[C:8]([C:10]([O:12]C)=[O:11])[C:7]([O:14][CH3:15])=[N:6][C:5]=1[NH:16][CH2:17][CH3:18].Cl>O>[Cl:3][C:4]1[N:9]=[C:8]([C:10]([OH:12])=[O:11])[C:7]([O:14][CH3:15])=[N:6][C:5]=1[NH:16][CH2:17][CH3:18]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 21418994Methyl 5-ethylamino-6-chloro-3-methoxypyrazine-2-carboxylate

Product 1

HCID 214190816-Chloro-5-ethylamino-3-methoxypyrazine-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In a solution of 18.7 g. of sodium hydroxide in 400 ml. of water was suspended 104 g. of methyl 6-chloro-5-ethylamino-3-methoxypyrazine-2-carboxylate and the suspension was stirred for 15 hours at room temperature to give a homogeneous solution. The solution was acidified with 80 ml. of an aqueous 18% hydrochloric acid solution and then allowed to stand for 2 hours at 5°-10° C. The crystals formed were recovered by filtration, washed with water and dried over anhydrous phosphorous pentoxide under reduced pressure to provide 92.5 of 6-chloro-5-ethylamino-3-methoxypyrazine-2-carboxylic acid. Melting point 166.5°-166° C. (recrystallized from chloroform).

Workup

  1. customto give a homogeneous solution
  2. customThe crystals formed
  3. filtrationwere recovered by filtration
  4. washwashed with water
  5. dry with materialdried over anhydrous phosphorous pentoxide under reduced pressure

Sources & evidence

ORD record
ord-1a734140e2a144448f85e59003d5a950
Source dataset
uspto-grants-1977_08
Patent number
US04041032

Reaction notes

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