3-Aminopyridine → Phenyl pyridin-3-ylcarbamate

HRID 655119Notes

Reaction equation

HRID 655119 reaction equation
Cl[C:2]([O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:3].[NH2:11][C:12]1[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=1>N1C=CC=CC=1.C(Cl)Cl.C(Cl)Cl>[C:5]1([O:4][C:2](=[O:3])[NH:11][C:12]2[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=2)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

5

Reactant 2

HCID 100093-AminopyridineHCID 15891Phenyl chloroformate

Product 1

HCID 6935890Phenyl pyridin-3-ylcarbamate

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 21875418Pyridine methylene chlorideSolvent

Conditions

Temperature
0 °C

Procedure

Phenyl chloroformate (0.733 mL, 5.84 mmol) is suspended in pyridine/DCM (3 mL, 2:1). The solution is stirred at 0° C., and 3-aminopyridine (500 mg, 5.31 mmol) dissolved in DCM (1 mL) is added dropwise. The reaction mixture is at 0° C. for 1 hour. The solvent is removed in vacuo and the residue is dissolved in ethyl acetate. This organic portion is washed with 0.1 M HCl and then concentrated in vacuo to afford the titled compound. (MH+215)

Workup

  1. additionis added dropwise
  2. customThe solvent is removed in vacuo
  3. dissolutionthe residue is dissolved in ethyl acetate
  4. washThis organic portion is washed with 0.1 M HCl
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-71eaca85046140029a122e00aa02ab7e
Source dataset
uspto-grants-2011_12
Patent number
US08071565B2

Reaction notes

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