Cyclopropylamine → HCID 29564077, compound

HRID 2390878Notes

Reaction equation

HRID 2390878 reaction equation
[CH2:1]([O:3][C:4](=[O:12])[C:5]1[CH:10]=[CH:9][C:8](Cl)=[N:7][CH:6]=1)[CH3:2].[CH:13]1([NH2:16])[CH2:15][CH2:14]1>CCOC(C)=O>[CH:13]1([NH:16][C:8]2[CH:9]=[CH:10][C:5]([C:4]([O:3][CH2:1][CH3:2])=[O:12])=[CH:6][N:7]=2)[CH2:15][CH2:14]1

Participants

4

Reactant 2

HCID 69828CyclopropylamineHCID 2799611Ethyl 6-chloronicotinate

Product 1

HCID 29564077HCID 29564077, compoundYield 63.9%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A microwave vial is charged with ethyl-6-chloronicotinate (1 g, 5.39 mmol) and cyclopropylamine (1 mL, 14.43 mmol), sealed and stirred at 80° overnight. After cooling to RT, the yellow solid was stirred with EtOAc and filtered. The filtrate was preadsorbed on SiO2 and applied to the top of a SiO2 column and eluted with an EtOAc/hexane gradient (0 to 30% EtOAc) to afford 0.71 g of ethyl 6-cyclopropylamino-nicotinoate (332) as an off white solid (17).

Workup

  1. customsealed
  2. filtrationfiltered
  3. washeluted with an EtOAc/hexane gradient (0 to 30% EtOAc)

Sources & evidence

ORD record
ord-33baca0293244582a1430c9761477cc2
Source dataset
uspto-grants-2012_09
Patent number
US08273773B2

Reaction notes

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