Triethylamine → HCID 2800351, compound

HRID 973927Notes

Reaction equation

HRID 973927 reaction equation
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[NH2:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=1.C(N(CC)CC)C>C(O)C>[N+:8]([C:7]1[C:2]([NH:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=2)=[N:3][CH:4]=[CH:5][CH:6]=1)([O-:10])=[O:9]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 195092-PyridinemethanamineHCID 796132-Chloro-3-nitropyridine

Product 1

HCID 2800351HCID 2800351, compoundYield 95.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of 2-chloro-3-nitropyridine (26.56 g, 0.168 mol) in absolute ethanol (250 mL) was added 2-(aminomethyl)pyridine (20.0 g, 0.185 mol) and triethylamine (16.99 g, 0.168 mol). The solution was heated at reflux for 2 hr and evaporated under reduced pressure. The residue was triturated in ethyl acetate several times and filtered. The filtrate was washed 3 times with a saturated sodium chloride solution, dried (sodium sulfate), filtered and evaporated under reduced pressure to give 36.8 g of N-(3-nitro-2-pyridinyl)-2-pyridinemethanamine (95% yield). A 1.0 g portion of the solid was recrystallized from isopropyl ether and dried under high vacuum to give 0.57 g of N-(3-nitro-2-pyridinyl)-2-pyridinemethanamine, mp 112°-115° C.

Workup

  1. temperatureThe solution was heated
  2. temperatureat reflux for 2 hr
  3. customevaporated under reduced pressure
  4. customThe residue was triturated in ethyl acetate several times
  5. filtrationfiltered
  6. washThe filtrate was washed 3 times with a saturated sodium chloride solution
  7. dry with materialdried (sodium sulfate)
  8. filtrationfiltered
  9. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-b5d619a2c8494082be77a834d242b720
Source dataset
uspto-grants-1991_11
Patent number
US05066654

Reaction notes

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