3-Aminopyridine → Phenyl pyridin-3-ylcarbamate

HRID 2382372Notes

Reaction equation

HRID 2382372 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 drop-wise. 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 0.1M HCl and then concentrated in vacuo to afford the titled compound. (MH+ 215).

Workup

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

Sources & evidence

ORD record
ord-f7a6a5bcfd234c289b214f3209cc7949
Source dataset
uspto-grants-2012_09
Patent number
US08258141B2

Reaction notes

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