4-Aminopyridine → Ethyl 4-pyridinylcarbamate

HRID 1379661Notes

Reaction equation

HRID 1379661 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)

Sources & evidence

ORD record
ord-551dac6b30d64936a76cef50d9e3f766
Source dataset
uspto-grants-1997_09
Patent number
US05672611

Reaction notes

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