3-Aminopyridine → Phenyl pyridin-3-ylcarbamate

HRID 1882525Notes

Reaction equation

HRID 1882525 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-9fc25f1d687742bd8a5cb9998528918d
Source dataset
uspto-grants-2012_11
Patent number
US08318750B2

Reaction notes

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