Sodium Hydroxide → 3-Amino-6-chloro-pyrazine-2-carboxylic acid

HRID 971624Notes

Reaction equation

HRID 971624 reaction equation
[NH2:1][C:2]1[C:7]([C:8]([O:10]C)=[O:9])=[N:6][C:5]([Cl:12])=[CH:4][N:3]=1.[OH-].[Na+]>>[NH2:1][C:2]1[C:7]([C:8]([OH:10])=[O:9])=[N:6][C:5]([Cl:12])=[CH:4][N:3]=1

Participants

3

Reactant 2

HCID 14798Sodium HydroxideHCID 824637Methyl 3-amino-6-chloropyrazine-2-carboxylate

Product 1

HCID 123191853-Amino-6-chloro-pyrazine-2-carboxylic acid

Procedure

One of the intermediates, 2-amino-5-chloropyrazine is prepared following the general procedure of Palamidessi and Bernardi, J. Org. Chem. 29, 2491 (1964), wherein methyl 2-amino-3-pyrazinylcarboxylate is allowed to react with chlorine in acetic acid to yield methyl 2-amino-5-chloro-3-pyrazinylcarboxylate. This ester is hydrolyzed with aqueous sodium hydroxide to yield 2-amino-3-carboxy-5-chloropyrazine, which is then heated in tetrahydronaphthalene and decarboxylated to yield the desired 2-amino-5-chloropyrazine.

Sources & evidence

ORD record
ord-6596406752394cbeb43bf20c5de47500
Source dataset
uspto-grants-1979_07
Patent number
US04160834

Reaction notes

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