Ethyl Acetate → Methyl 5-(pyrrol-1-yl)-3-pyridinecarboxylate

HRID 399802Notes

Reaction equation

HRID 399802 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:8]([O:10][CH3:11])=[O:9])[CH:5]=[N:6][CH:7]=1.CO[CH:14]1[CH2:18][CH2:17][CH:16](OC)O1.C(OCC)(=O)C.C(=O)([O-])[O-].[K+].[K+]>C(O)(=O)C.O>[N:1]1([C:2]2[CH:3]=[C:4]([C:8]([O:10][CH3:11])=[O:9])[CH:5]=[N:6][CH:7]=2)[CH:14]=[CH:18][CH:17]=[CH:16]1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 790982,5-DimethoxytetrahydrofuranHCID 1514432Methyl 5-aminopyridine-3-carboxylate

Product 1

HCID 18945279Methyl 5-(pyrrol-1-yl)-3-pyridinecarboxylateYield 57.1%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

A mixture of methyl 5-amino-3-pyridinecarboxylate (1.7 g) and 2.5-dimethoxytetrahydrofuran (2.2 g) in acetic acid (5 ml) was refluxed for 30 minutes. After being cooled to room temperature, the reaction mixture was poured into a mixture of ethyl acetate (50 ml) and water (50 ml) under stirring, and adjusted to pH 8.5 with 10% potassium carbonate aqueous solution. The organic layer was washed with brine and dried over magnesium sulfate. The solvent was evaporated in vacuo and the residue was recrystallized from diethyl ether-n-hexane to afford methyl 5-(pyrrol-1-yl)-3-pyridinecarboxylate (1.29 g).

Workup

  1. temperaturewas refluxed for 30 minutes
  2. washThe organic layer was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. customThe solvent was evaporated in vacuo
  5. customthe residue was recrystallized from diethyl ether-n-hexane

Sources & evidence

ORD record
ord-293309cc602b4c708dcc6beba7efb024
Source dataset
uspto-grants-1998_10
Patent number
US05824691

Reaction notes

Loading…