Ethylene Glycol → 2-Amino-5-(4-bromophenyl)-6-methylpyrazine

HRID 128143

Reaction equation

HRID 128143 reaction equation
C(O)CO.[NH2:5][C:6]1[C:11](C(O)=O)=[N:10][C:9]([C:15]2[CH:20]=[CH:19][C:18]([Br:21])=[CH:17][CH:16]=2)=[C:8]([CH3:22])[N:7]=1>[OH-].[Na+].C1C2C(=CC=CC=2)CCC1>[NH2:5][C:6]1[CH:11]=[N:10][C:9]([C:15]2[CH:16]=[CH:17][C:18]([Br:21])=[CH:19][CH:20]=2)=[C:8]([CH3:22])[N:7]=1

Participants

5

Reactant 2

HCID 174Ethylene GlycolHCID 205670432-Amino-3-carboxy-5-(4-bromophenyl)-6-methylpyrazine

Product 1

HCID 127956102-Amino-5-(4-bromophenyl)-6-methylpyrazine

Reagents, catalysts & solvents 2

HCID 8404TetralinSolventHCID 14798Sodium HydroxideSolvent

Procedure

Another intermediate pyrazine compound, 2-amino-5-(4-bromophenyl)-6-methylpyrazine is synthesized starting with 1-(4-bromophenyl)-1,2-propanedione 2-oxime, which oxime is obtained by the same general procedure of Hartung et al., supra. This oxime is allowed to react with aminomalononitrile tosylate, and the product, the substituted pyrazine 1-oxide, is allowed to react with phosphoruc trichloride in tetrahydrofuran, according to the procedure of Taylor et al., J. Org. Chem. 38, 2817 (1973), to yield 2-amino-3-cyano-5-(4-bromophenyl)-6-methylpyrazine. This product is then hydrolyzed in sodium hydroxide and ethylene glycol and the 2-amino-3-carboxy-5-(4-bromophenyl)-6-methylpyrazine so obtained is decarboxylated by heating in tetrahydronaphthalene to yield 2-amino-5-(4-bromophenyl)-6-methylpyrazine.

Sources & evidence

ORD record
ord-8926dc01d739424992b25cfa9d91e7a4
Source dataset
uspto-grants-1981_03
Patent number
USRE030563

Linked notes

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