Nitric Acid → 7-nitro-5H-pyrrolo[2,3-b]pyrazine

HRID 1642092Notes

Reaction equation

HRID 1642092 reaction equation
[N:1]1[CH:6]=[CH:5][N:4]=[C:3]2[NH:7][CH:8]=[CH:9][C:2]=12.[N+:10]([O-])([OH:12])=[O:11].C(=O)(O)[O-].[Na+]>O>[N+:10]([C:9]1[C:2]2[C:3](=[N:4][CH:5]=[CH:6][N:1]=2)[NH:7][CH:8]=1)([O-:12])=[O:11]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 516892Sodium BicarbonateHCID 53708035H-Pyrrolo[2,3-b]pyrazine

Product 1

HCID 122071927-nitro-5H-pyrrolo[2,3-b]pyrazine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

7-Nitro-5H-pyrrolo[2,3-b]pyrazine (5) is prepared by adding 5H-pyrrolo[2,3-b]pyrazine (3) to fuming nitric acid while cooling (e.g. 0° C.). After stirring for one to several hours, water is carefully added and the mixture neutralized with saturated sodium bicarbonate. The solids are collected by filtration and dried to provide 7-nitro-5H-pyrrolo[2,3-b]pyrazine 5.

Workup

  1. custom7-Nitro-5H-pyrrolo[2,3-b]pyrazine (5) is prepared
  2. additionis carefully added
  3. filtrationThe solids are collected by filtration
  4. customdried

Sources & evidence

ORD record
ord-154cf4acfdd640b3a18fb50da19058f6
Source dataset
uspto-grants-2012_02
Patent number
US08119637B2

Reaction notes

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