Sodium Hydroxide → 8-Nitropyrrolo[1,2-a]pyrazine

HRID 233459

Reaction equation

HRID 233459 reaction equation
[CH:1]1[C:2]2[N:3]([CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:5][N:6]=1.S(=O)(=O)(O)O.[N+:15]([O-])([OH:17])=[O:16].[OH-].[Na+]>C(O)(=O)C>[N+:15]([C:9]1[CH:8]=[CH:7][N:3]2[CH:4]=[CH:5][N:6]=[CH:1][C:2]=12)([O-:17])=[O:16]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 11018843Pyrrolo(1,2-a)pyrazineHCID 71777668Sulfuric acid, mixt. with nitric acid

Product 1

HCID 233564328-Nitropyrrolo[1,2-a]pyrazine

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

5.5 g of pyrrolo[1,2-a]pyrazine prepared in Preparation Example 1 was dissolved in 10 ml of glacial acetic acid; and to the resulting mixture was added dropwise a mixture of sulfuric acid/nitric acid (15 ml/15 ml) at 0° C. The reaction mixture was stirred at room temperature for 30 minutes, poured into 200 ml of ice-water, and then adjusted to pH 10 with sodium hydroxide solution. The resulting solution was extracted with ethyl acetate (100 ml×3), and concentrated to dryness to obtain 4.3 g of title compound.

Workup

  1. additionand to the resulting mixture was added dropwise
  2. extractionThe resulting solution was extracted with ethyl acetate (100 ml×3)
  3. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-905c6bb533cd4d72b1b7e1b71c45a935
Source dataset
uspto-grants-1997_01
Patent number
US05593984

Linked notes

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