Pyridine → Phenyl pyridin-3-ylcarbamate

HRID 1882537Notes

Reaction equation

HRID 1882537 reaction equation
N1C=CC=CC=1.[C:7]1([O:13][C:14](Cl)=[O:15])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[NH2:17][C:18]1[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=1>C(Cl)Cl>[C:7]1([O:13][C:14](=[O:15])[NH:17][C:18]2[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 100093-AminopyridineHCID 15891Phenyl chloroformate

Product 1

HCID 6935890Phenyl pyridin-3-ylcarbamate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of pyridine (2 ml) in DCM (10 ml) is treated with phenylchloroformate (1.83 g, 11.7 mmol). To this solution is added 3-aminopyridine (1.0 g, 10.6 mmol) in DCM (8 ml) which results in an exotherm of 20° C. The reaction mixture is stirred at room temperature for 2 hours and then concentrated in vacuo. The residue is partitioned between EtOAc and water and the organic portion is separated. This organic portion is washed with water, saturated sodium bicarbonate solution, dried (MgSO4) and concentrated in vacuo to afford the title compound as a white solid. (MH+ 215.13)

Workup

  1. customresults in an exotherm of 20° C
  2. concentrationconcentrated in vacuo
  3. customThe residue is partitioned between EtOAc and water
  4. customthe organic portion is separated
  5. washThis organic portion is washed with water, saturated sodium bicarbonate solution
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0347db1a3a9f4911aeeb161d8fafebfb
Source dataset
uspto-grants-2012_11
Patent number
US08318750B2

Reaction notes

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