4-Aminopyridine → Ammonia

HRID 1982797Notes

Reaction equation

HRID 1982797 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1.Cl[C:9]([O:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:10]>C1COCC1.CCOC(C)=O>[NH3:1].[C:12]1([O:11][C:9](=[O:10])[NH:1][C:2]2[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 2

HCID 17274-AminopyridineHCID 15891Phenyl chloroformate

Product 2

HCID 222AmmoniaYield 0%HCID 11401617Carbamic acid, 4-pyridinyl-, phenyl ester

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of 4-aminopyridine (0.941 g) in THF (10 mL) was added dropwise phenyl chloroformate (2×0.25 mL) at 0° C. The mixture was allowed to warm to rt overnight. The mixture was diluted with EtOAc (30 mL) and washed with saturated (satd.) aq. NaHCO3. The organic layer was dried (MgSO4) and concentrated. Chromatography of the residue (0-5% 2 M NH3 in MeOH-DCM) gave a the title compound as a white solid (0.74 g).

Workup

  1. washwashed with saturated (satd.) aq. NaHCO3
  2. dry with materialThe organic layer was dried (MgSO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-2c080ccb8c104c3c989ae704d0cf90b9
Source dataset
uspto-grants-2009_06
Patent number
US07541359B2

Reaction notes

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