Benzylamine → HCID 21882767, compound

HRID 722063Notes

Reaction equation

HRID 722063 reaction equation
F[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[C:6]([O:11][CH2:12][CH2:13][O:14][CH3:15])[CH:5]=[CH:4][N:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:22]([NH2:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>CN1CCCC1=O.O>[CH2:22]([NH:29][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[C:6]([O:11][CH2:12][CH2:13][O:14][CH3:15])[CH:5]=[CH:4][N:3]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

6

Reactant 3

HCID 7504BenzylamineHCID 11430Potassium CarbonateHCID 21882713HCID 21882713, compound

Product 1

HCID 21882767HCID 21882767, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

2.32 g of 2-fluoro-4-(2-methoxyethoxy)-3-nitropyridine (starting material J3), 4.44 g of potassium carbonate and 1.11 ml of benzylamine in 25 ml of N-methylpyrrolidone are stirred at room temperature for 5 hours. The mixture is diluted with water and then extracted twice with diethylether. The combined ether phases are washed with with water and brine and are then concentrated in vacuo. The residue is chromatographed on silica gel (ethyl acetate/petroleum ether 1:2). Concentration of the pure fractions and drying in vacuo gives 2.0 g of the title compound as a yellow oil, which crystallizes on standing (m.p. 81–83° C.). The mass spectrum shows the molecular peak MH+ at 304.0 Da.

Workup

  1. extractionextracted twice with diethylether
  2. washThe combined ether phases are washed with with water and brine
  3. concentrationare then concentrated in vacuo
  4. customThe residue is chromatographed on silica gel (ethyl acetate/petroleum ether 1:2)
  5. customConcentration of the pure fractions and drying in vacuo

Sources & evidence

ORD record
ord-6252bbe2622f4354a85743d914fbf9bf
Source dataset
uspto-grants-2006_11
Patent number
US07138399B2

Reaction notes

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