Sodium Carbonate → N-(3-nitro-2-pyridinyl)-2-pyrazinemethanamine

HRID 1533954Notes

Reaction equation

HRID 1533954 reaction equation
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1.Cl.Cl.[N:13]1[CH:18]=[CH:17][N:16]=[CH:15][C:14]=1[CH2:19][NH2:20].CN(C)C(=O)C.C(=O)([O-])[O-].[Na+].[Na+]>CC(C)CC(=O)C.O>[N+:8]([C:7]1[C:2]([NH:20][CH2:19][C:14]2[CH:15]=[N:16][CH:17]=[CH:18][N:13]=2)=[N:3][CH:4]=[CH:5][CH:6]=1)([O-:10])=[O:9]

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 31374DimethylacetamideHCID 796132-Chloro-3-nitropyridineHCID 19911503Pyrazin-2-ylmethanamine dihydrochloride

Product 1

HCID 17845733N-(3-nitro-2-pyridinyl)-2-pyrazinemethanamineYield 10%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 7909Methyl Isobutyl KetoneSolvent

Conditions

Temperature
100 °C

Procedure

To a stirred solution of 25.4 parts of 2-chloro-3-nitropyridine, 29.5 parts of 2-pyrazinemethanamine dihydrochloride and 235 parts of N,N-dimethylacetamide were added 67.8 parts of sodium carbonate. The reaction mixture was stirred for 1.5 hours at 100° C. The reaction mixture was poured into water and 4-methyl-2-pentanone. The whole was filtered twice over diatomaceous earth and the layers were separated. The organic layer was dried, filtered and evaporated. The residue was crystallized from acetonitrile. The product was filtered off and dried, yielding 3.6 parts (10%) of N-(3-nitro-2-pyridinyl)-2-pyrazinemethanamine (int. 27).

Workup

  1. filtrationThe whole was filtered twice over diatomaceous earth
  2. customthe layers were separated
  3. customThe organic layer was dried
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was crystallized from acetonitrile
  7. filtrationThe product was filtered off
  8. customdried

Sources & evidence

ORD record
ord-4d5aa872477f4973a8e725d49ce781e4
Source dataset
uspto-grants-1992_02
Patent number
US05086056

Reaction notes

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