Water → 6-chloro-N-(1,3-dioxolan-2-ylmethyl)-3-nitropyridin-2-amine

HRID 385518Notes

Reaction equation

HRID 385518 reaction equation
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[C:4]([Cl:11])[N:3]=1.C(=O)([O-])[O-].[K+].[K+].[NH2:18][CH2:19][CH:20]1[O:24][CH2:23][CH2:22][O:21]1.O>C(#N)C.C(OCC)(=O)C>[Cl:11][C:4]1[N:3]=[C:2]([NH:18][CH2:19][CH:20]2[O:24][CH2:23][CH2:22][O:21]2)[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=1

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 852392,6-Dichloro-3-nitropyridineHCID 108553941-(1,3-Dioxolan-2-yl)methanamine2×

Product 1

HCID 578153716-chloro-N-(1,3-dioxolan-2-ylmethyl)-3-nitropyridin-2-amine

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 0.50 g of 2,6-dichloro-3-nitropyridine in 5 mL of acetonitrile, 0.43 g of potassium carbonate was added, thereto was added a solution of 0.24 mL of 2-aminomethyl-1,3-dioxolan in 3 mL of acetonitrile under cooling with ice, and the mixture was stirred for 2 hours under cooling with ice. Thereto was further added 80 μL of 2-aminomethyl-1,3-dioxolan, and the mixture was stirred for 2 hours under cooling with ice. Water and ethyl acetate were added thereto under cooling with ice, the organic layer was separated, washed with a saturated aqueous sodium chloride solution and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The resultant residue was purified by basic silica gel column chromatography using an eluent of hexane:ethyl acetate=20:1 to obtain 0.44 g of 6-chloro-N-(1,3-dioxolan-2-ylmethyl)-3-nitropyridin-2-amine as a yellow solid.

Workup

  1. temperatureunder cooling with ice
  2. temperatureunder cooling with ice
  3. stirringthe mixture was stirred for 2 hours
  4. temperatureunder cooling with ice
  5. temperatureunder cooling with ice
  6. customthe organic layer was separated
  7. washwashed with a saturated aqueous sodium chloride solution
  8. dry with materialdried over anhydrous sodium sulfate
  9. distillationthe solvent was distilled off under reduced pressure
  10. customThe resultant residue was purified by basic silica gel column chromatography

Sources & evidence

ORD record
ord-795a84c8fba54e1688a804a010314011
Source dataset
uspto-grants-2013_02
Patent number
US08367831B2

Reaction notes

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