Sodium Hydroxide → HCID 178441333, compound

HRID 1655577Notes

Reaction equation

HRID 1655577 reaction equation
[CH2:1]([C:5]1[N:6]=[C:7]([OH:14])[C:8]([C:11](N)=[O:12])=[N:9][CH:10]=1)[CH2:2][CH2:3][CH3:4].[OH-:15].[Na+]>O>[CH2:1]([C:5]1[N:6]=[C:7]([OH:14])[C:8]([C:11]([OH:15])=[O:12])=[N:9][CH:10]=1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 178441328HCID 178441328, compound

Product 1

HCID 178441333HCID 178441333, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2-Oxohexanal (F. Ballistreri, et al., J. Organic Chem., 53, 830 (1988) is reacted (according to the method described by F. L. Muehlmann and A. R. Day in J. American Chem. Soc., 78, 242-4(1956) substituting 2-oxohexanal for the 2-oxopropanal used in the synthesis of 5-methyl-3-hydroxypyrazine-2-carboxamide) with aminomalonamide to give 5-n-butyl-3-hydroxypyrazine-2-carboxamide. The amide is hydrolyzed with sodium hydroxide in water at 95° C. to give 5-n-butyl-3-hydroxypyrazine-2-carboxylic acid. The acid is converted to the corresponding ester with methanol and hydrochloric acid and the ester is chlorinated with phosphorous oxychloride (according to the method described by G. Dick and H. Wood in J. Chem. Soc., 1955, 1379-82) to give the title compound.

Sources & evidence

ORD record
ord-135f9f15fefe411e87f91eef05d9db46
Source dataset
uspto-grants-1993_10
Patent number
US05250548

Reaction notes

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