2-Aminopropanediamide → HCID 178513793, compound

HRID 1995058Notes

Reaction equation

HRID 1995058 reaction equation
O.[C:2]1([C:8]([CH:10]=O)=O)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(=O)(O)[O-].[Na+].[NH2:17][CH:18]([C:22]([NH2:24])=[O:23])[C:19]([NH2:21])=[O:20]>O>[OH:20][C:19]1[C:18]([C:22]([NH2:24])=[O:23])=[N:17][CH:10]=[C:8]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[N:21]=1

Participants

5

Reactant 3

HCID 964572-AminopropanediamideHCID 12215922Glyoxal, phenyl-, hydrateHCID 23665763Sodium Bisulfite

Product 1

HCID 178513793HCID 178513793, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
100 °C

Procedure

A solution of 5.4 g. of phenylglyoxal hydrate in 25 ml. water is treated with 50 ml. of aqueous sodium bisulfite (density 1.34) at 25° C. for 45 min. A solution of 3.9 g. of aminomalonamide in 39 ml. of water is added and the reaction mixture is heated at 100° C. for 2.5 hr. The resultant yellow precipitate which forms is isolated by filtration, washed with water, dried and recrystallized from ethanol to afford 3-hydroxy-5-phenylpyrazine-2-carboxamide. This product is hydrolyzed with saturated ethanolic sodium hydroxide for 16 hrs. at 150° C. to afford 3-hydroxy-5-phenylpyrazine-2-carboxylic acid. This product is refluxed with 30 ml. of carbitolacetate for 15 min. then cooled to 250° C. and petroleum ether (bp 68° C.) added to precipitate the title compound.

Workup

  1. customThe resultant yellow precipitate which forms is isolated by filtration
  2. washwashed with water
  3. customdried
  4. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-3ada3cb555594d858bc2cc75fd4635ec
Source dataset
uspto-grants-1983_09
Patent number
US04402958

Reaction notes

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