Water → N-(cyclopropylmethyl)-3-nitropyridin-2-amine

HRID 1913080Notes

Reaction equation

HRID 1913080 reaction equation
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[CH:11]1([CH2:14][NH2:15])[CH2:13][CH2:12]1.O>O1CCCC1>[CH:11]1([CH2:14][NH:15][C:2]2[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=2)[CH2:13][CH2:12]1

Participants

5

Reactant 3

HCID 962WaterHCID 75646CyclopropanemethanamineHCID 796132-Chloro-3-nitropyridine

Product 1

HCID 29766774N-(cyclopropylmethyl)-3-nitropyridin-2-amineYield 95.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3 g (18.9 mM) of 2-chloro-3-nitropyridine and 5 g (70.3 mM) of cyclopropylmethylamine in 12 ml of tetrahydrofurane were refluxed under stirring for 1 h. Water was added and the aqueous layer was extracted with ethylacetate. The organic layer was washed with water and dried over anhydrous sodium sulfate. The solvent was removed under vacuum to give 3.5 g of N-(cyclopropylmethyl)-3-nitropyridin-2-amine as a yellow oil. Yield: 95%.

Workup

  1. extractionthe aqueous layer was extracted with ethylacetate
  2. washThe organic layer was washed with water
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was removed under vacuum

Sources & evidence

ORD record
ord-9a0d6b238f464e45b4ccdd8168cfb4c1
Source dataset
uspto-grants-2013_12
Patent number
US08609689B2

Reaction notes

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