Acetonitrile → HCID 70335437, compound

HRID 2284687Notes

Reaction equation

HRID 2284687 reaction equation
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[C:11]([O:15][C:16](=[O:22])[NH:17][CH2:18][CH2:19][CH2:20][NH2:21])([CH3:14])([CH3:13])[CH3:12].C(=O)([O-])[O-].[K+].[K+].C(#N)C>O.C(OCC)(=O)C>[N+:8]([C:7]1[C:2]([NH:21][CH2:20][CH2:19][CH2:18][NH:17][C:16](=[O:22])[O:15][C:11]([CH3:13])([CH3:12])[CH3:14])=[N:3][CH:4]=[CH:5][CH:6]=1)([O-:10])=[O:9]

Participants

7

Reactant 4

HCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 796132-Chloro-3-nitropyridineHCID 2735700tert-Butyl (3-aminopropyl)carbamate

Product 1

HCID 70335437HCID 70335437, compoundYield 108.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To 2-chloro-3-nitropyridine (92 mg), tert-butyl(3-aminopropyl)carbamate (102 mg) and potassium carbonate (161 mg), acetonitrile (1.2 mL) was added at room temperature, and the mixture was stirred at the same temperature for 4 hours. To the reaction mixture, ethyl acetate and water were added. The organic layer was separated, washed with saturated aqueous sodium chloride, and then dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (eluent, 100 to 0% hexane in ethyl acetate) to obtain tert-butyl (3-((3-nitropyridin-2-yl)amino)propyl)carbamate (C42, 186 mg).

Workup

  1. customThe organic layer was separated
  2. washwashed with saturated aqueous sodium chloride
  3. dry with materialdried over anhydrous sodium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (eluent, 100 to 0% hexane in ethyl acetate)

Sources & evidence

ORD record
ord-7dbb34eaf6a948dcbc249d6272a371db
Source dataset
uspto-grants-2015_09
Patent number
US09145415B2

Reaction notes

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