4-Aminopyridine → Ethyl 4-pyridinylcarbamate

HRID 840257Notes

Reaction equation

HRID 840257 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1.Cl[C:9]([O:11][CH2:12][CH3:13])=[O:10]>N1C=CC=CC=1.C(Cl)Cl>[CH2:12]([O:11][C:9]([NH:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1)=[O:10])[CH3:13]

Participants

5

Reactant 2

HCID 17274-AminopyridineHCID 10928Ethyl chloroformate

Product 1

HCID 766500Ethyl 4-pyridinylcarbamateYield 33.3%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

4-Aminopyridine (17.34 grams) (184.3) was dissolved in dry pyridine (217 ml.) and cooled to 0° C. over 30 minutes. Ethyl chloroformate (17.2 ml.) (180.7 mmoles) was added and the solution was stirred at 0° C. for 1 hour and then at 25° C. for 40 hours. The mixture was diluted with CH2Cl2 and washed with saturated aqueous NaHCO3 and water. The CH2Cl2 was dried (MgSO4), filtered and evaporated to dryness. The residue was chromatographed on silica gel using 2% (10% saturated NH4OH in MeOH)—CH2Cl2 to give the title compound (Yield: 10 grams, 33%, M+ 166).

Workup

  1. waitat 25° C. for 40 hours
  2. washwashed with saturated aqueous NaHCO3 and water
  3. dry with materialThe CH2Cl2 was dried (MgSO4)
  4. filtrationfiltered
  5. customevaporated to dryness
  6. customThe residue was chromatographed on silica gel using 2% (10% saturated NH4OH in MeOH)—CH2Cl2

Sources & evidence

ORD record
ord-4b366cafa30a475887a1236c6655e7a9
Source dataset
uspto-grants-2002_04
Patent number
US06365588B1

Reaction notes

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