Dimethyl 5-aminoisophthalate → 1,3-Dimethyl 5-(1H-pyrrol-1-yl)-1,3-benzenedicarboxylate
Reaction equation
CO[CH:3]1[CH2:7][CH2:6][CH:5](OC)O1.[NH2:10][C:11]1[CH:12]=[C:13]([C:21]([O:23][CH3:24])=[O:22])[CH:14]=[C:15]([CH:20]=1)[C:16]([O:18][CH3:19])=[O:17]>C(O)(=O)C>[N:10]1([C:11]2[CH:20]=[C:15]([C:16]([O:18][CH3:19])=[O:17])[CH:14]=[C:13]([CH:12]=2)[C:21]([O:23][CH3:24])=[O:22])[CH:3]=[CH:7][CH:6]=[CH:5]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 135 °C
Procedure
2,5-dimethoxytetrahydrofuran (0.74 ml, 0.76 g, 5.74 mmol, 1.2 eq) was added to a stirred suspension of dimethyl 5-aminoisophthalate (1.0 g, 4.78 mmol, 1 eq) in 7 ml acetic acid under Ar. The mixture was heated to reflux at 135° C. After 45 min the reaction was cooled to RT, and the solvent was removed in vacuo. The residue was stirred in saturated aqueous NaHCO3/EtOAc overnight. The layers were separated. The organic layer was washed with saturated aqueous NaHCO3 (×1), water (×2), brine (×1), and dried over Na2SO4. The inorganics were filtered off, and the solvent was removed in vacuo. Purification via flash chromatography yielded 0.288 g (1.11 mmol, 23% yield) of the product. A significant amount of crude product was also collected.