Dimethyl 5-aminoisophthalate → 1,3-Dimethyl 5-(1H-pyrrol-1-yl)-1,3-benzenedicarboxylate

HRID 2071137Notes

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]1

Participants

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.

Workup

temperatureThe mixture was heated
temperatureAfter 45 min the reaction was cooled to RT
customthe solvent was removed in vacuo
customThe layers were separated
washThe organic layer was washed with saturated aqueous NaHCO3 (×1), water (×2), brine (×1)
dry with materialdried over Na2SO4
filtrationThe inorganics were filtered off
customthe solvent was removed in vacuo
customPurification via flash chromatography

Sources & evidence

ORD record: ord-0734fe30bbcc410a814a58f2832283d6
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08299267B2

Reaction notes

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