Cyclopropylamine → Ethyl 2-(cyclopropylcarbamoyl)pyridine-4-carboxylate

HRID 714452Notes

Reaction equation

HRID 714452 reaction equation
C(O[C:4]([C:6]1[CH:11]=[C:10]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:9]=[CH:8][N:7]=1)=[O:5])C.[Cl-].[Mg+2].[Cl-].[CH:20]1([NH2:23])[CH2:22][CH2:21]1>C(O)C>[CH:20]1([NH:23][C:4]([C:6]2[CH:11]=[C:10]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:9]=[CH:8][N:7]=2)=[O:5])[CH2:22][CH2:21]1

Participants

5

Reactant 3

HCID 69828CyclopropylamineHCID 170509Diethyl 2,4-pyridinedicarboxylateHCID 5360315Magnesium Chloride

Product 1

HCID 66631638Ethyl 2-(cyclopropylcarbamoyl)pyridine-4-carboxylate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

5.5 g (24.64 mmol) of diethylpyridine 2,4-dicarboxylate (Example 50A) were dissolved in 55 ml of ethanol. 0.47 g (4.93 mmol) of magnesium chloride was added, and the mixture was then cooled to 0° C., 8.44 g (147.83 mmol) of cyclopropylamine were slowly added dropwise and the reaction mixture was stirred at 0° C. for 15 min and stirred further at RT for 2 days. The reaction mixture was evaporated. The residue was dissolved in water and extracted three times with ethyl acetate. The combined organic phases were dried over magnesium sulfate, filtered and concentrated using a rotary evaporator.

Workup

  1. stirringstirred further at RT for 2 days
  2. customThe reaction mixture was evaporated
  3. dissolutionThe residue was dissolved in water
  4. extractionextracted three times with ethyl acetate
  5. dry with materialThe combined organic phases were dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customa rotary evaporator

Sources & evidence

ORD record
ord-06fd0c6c0b334edab5b221f70013e5ae
Source dataset
uspto-grants-2015_11
Patent number
US09187428B2

Reaction notes

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