Cyclopentanone → 5H-Cyclopenta[c]pyridine-1-carboxylicacid,6,7-dihydro-,ethylester(9CI)

HRID 575846Notes

Reaction equation

HRID 575846 reaction equation
N1[CH:6]=[CH:5][N:4]=[C:3]([C:7]([O:9][CH2:10][CH3:11])=[O:8])N=1.[C:12]1(=O)[CH2:16][CH2:15][CH2:14][CH2:13]1.N1CCCC1>C1(C)C=CC=CC=1>[C:3]1([C:7]([O:9][CH2:10][CH3:11])=[O:8])[C:13]2[CH2:14][CH2:15][CH2:16][C:12]=2[CH:6]=[CH:5][N:4]=1

Participants

5

Reactant 3

HCID 8452CyclopentanoneHCID 31268PyrrolidineHCID 12559180Ethyl 1,2,4-triazine-3-carboxylate

Product 1

HCID 450986655H-Cyclopenta[c]pyridine-1-carboxylicacid,6,7-dihydro-,ethylester(9CI)Yield 25%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Ethyl 1,2,4-triazine-3-carboxylate (7 g, 45.8 mmol), cyclopentanone (4.9 mL, 55.0 mmol), and pyrrolidine (4.6 mL, 55.0 mmol) in toluene (100 mL) were heated to reflux for 12 h. The mixture was purified by column on silica gel chromatography (PE/EtOAc=5:1) to give the title compound (2.02 g, 25%) as a brown oil. LCMS: 192 (M+1)+

Workup

  1. temperatureto reflux for 12 h
  2. customThe mixture was purified by column on silica gel chromatography (PE/EtOAc=5:1)

Sources & evidence

ORD record
ord-89c18a4837e349e69afab6a135847481
Source dataset
uspto-grants-2015_05
Patent number
US09034900B2

Reaction notes

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