3-Amino-2-pyrazinecarboxylic acid → HCID 178524895, compound

HRID 1842506Notes

Reaction equation

HRID 1842506 reaction equation
N[C:2]1[C:3]([C:8]([OH:10])=[O:9])=[N:4][CH:5]=[CH:6][N:7]=1.N([O-])=[O:12].[Na+]>O.S(=O)(=O)(O)O>[OH:12][C:2]1[C:3]([C:8]([OH:10])=[O:9])=[N:4][CH:5]=[CH:6][N:7]=1

Participants

5

Reactant 2

HCID 726563-Amino-2-pyrazinecarboxylic acidHCID 23668193Sodium Nitrite

Product 1

HCID 178524895HCID 178524895, compoundYield 58,530.898%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1118Sulfuric AcidSolvent

Conditions

Temperature
50 °C

Procedure

The 3-amino-pyrazine-2-carboxylic acid (6.95 g, 0.05 mmol) was dissolved in a mixture of water (55 mL) and sulfuric acid (55 mL, 3.75M) and heated to 50° C. A solution of sodium nitrite (18.5 mL, 0.06 mmol) was added to the above solution which was cooled to 12° C. The temperature was maintained at 10-16° C. over 30 mins during addition period and then the mixture was heated to boiling over a period of 30 mins. After cooling to RT, the yellow solid was collected by filtration. The solid was dissolved in a dilute sodium bicarbonate solution, the carboxylic acid product precipitated by treatment with hydrochloric acid (10%) and collected by filtration, the crude carboxylic acid product was recrystallized from water to give a yellow-orange crystalline solid (4.1 g, yield 58%).

Workup

  1. temperaturewas cooled to 12° C
  2. temperatureThe temperature was maintained at 10-16° C. over 30 mins during addition period
  3. temperaturethe mixture was heated
  4. temperatureAfter cooling to RT
  5. filtrationthe yellow solid was collected by filtration
  6. dissolutionThe solid was dissolved in a dilute sodium bicarbonate solution
  7. customthe carboxylic acid product precipitated by treatment with hydrochloric acid (10%)
  8. filtrationcollected by filtration
  9. customthe crude carboxylic acid product was recrystallized from water

Sources & evidence

ORD record
ord-df4b4ac39f8146f59d24de51e3c2b067
Source dataset
uspto-grants-2015_02
Patent number
US08946230B2

Reaction notes

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