2-Chloro-3-nitropyridine → 6-methyl-N-(3-nitro-2-pyridinyl)-2pyridinemethanamine

HRID 2379039Notes

Reaction equation

HRID 2379039 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([CH2:8][NH2:9])[CH:5]=[CH:4][CH:3]=1.Cl[C:11]1[C:16]([N+:17]([O-:19])=[O:18])=[CH:15][CH:14]=[CH:13][N:12]=1.C(=O)([O-])O.[Na+]>C(O)C>[CH3:1][C:2]1[N:7]=[C:6]([CH2:8][NH:9][C:11]2[C:16]([N+:17]([O-:19])=[O:18])=[CH:15][CH:14]=[CH:13][N:12]=2)[CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 796132-Chloro-3-nitropyridineHCID 246721(6-Methylpyridin-2-yl)methanamineHCID 516892Sodium Bicarbonate

Product 1

HCID 189578416-methyl-N-(3-nitro-2-pyridinyl)-2pyridinemethanamineYield 51%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2.44 parts of 6-methyl-2-pyridinemethanamine, 3.2 parts of 2-chloro-3nitropyridine, 1.7 parts of sodium hydrogen carbonate and 120 parts of ethanol was stirred for 3 hours at reflux temperature. The reaction mixture was filtered while hot over diatomaceous earth. After cooling, the precipitate which formed in the tiltrate was filtered off and dried, yielding 2.5 parts (51%) of 6-methyl-N-(3-nitro-2-pyridinyl)-2pyridinemethanamine; mp. 131.7° C. (interm. 5).

Workup

  1. temperatureat reflux temperature
  2. filtrationThe reaction mixture was filtered while hot over diatomaceous earth
  3. temperatureAfter cooling
  4. customthe precipitate which formed in the tiltrate
  5. filtrationwas filtered off
  6. customdried

Sources & evidence

ORD record
ord-5aeaf342742b4e17819ec90bbd846c0c
Source dataset
uspto-grants-1994_11
Patent number
US05360807

Reaction notes

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