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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 506990Generated: November 3, 2026

Potassium Iodide → 3-[7-{2-[isopropyl(methyl)amino]ethoxy}-1-oxoisoquinolin-2(1H)-yl]-4-methylbenzoic acid

https://huagongshe.com/reaction/506990

Reaction equation

Participants

RoleNameHCIDCharge
ReactantPotassium IodideHCID 4875—
ReactantN-MethylisopropylamineHCID 78485—
ReactantDiisopropylethylamineHCID 81531—
ReactantIsocyanateHCID 105034—
Reactant3-[7-(2-chloroethoxy)-1-oxoisoquinolin-2(1H)-yl]-4-methylbenzoic acidHCID 67018595—
SolventDichloromethaneHCID 6344—
SolventDimethylacetamideHCID 31374—
Product3-[7-{2-[isopropyl(methyl)amino]ethoxy}-1-oxoisoquinolin-2(1H)-yl]-4-methylbenzoic acidHCID 67018593—

Reaction Steps

3-[7-(2-chloroethoxy)-1-oxoisoquinolin-2(1H)-yl]-4-methylbenzoic acid (504 mg), DIPEA (0.7 ml), potassium iodide (332 mg) and N-methylisopropylamine (0.42 ml) in DMA (4 ml) was heated under microwave irradiation conditions (Personal Chemistry Emrys Optimizer with 300 W magnetron) at 120° C. for 30 minutes. The mixture was diluted with methylene chloride (25 ml), isocyanate resin (CombiZorb) (7.67 g) was added and stirred at room temperature for 18 hours. The resin was removed by filtration and the filtrate was washed with water. The aqueous phase was purified by column chromatography on an ion exchange column (isolute SCX column from International Sorbent Technology Limited, Henoed, Mid-Glamorgan, UK) using initially methanol and then a 99:1 mixture of methanol and aqueous ammonia solution to yield 3-[7-{2-[isopropyl(methyl)amino]ethoxy}-1-oxoisoquinolin-2(1H)-yl]-4-methylbenzoic acid as a pale brown solid (110 mg); NMR Spectrum: (DMSOd6) 1.00 (m, 6H), 2.15 (s, 3H), 2.30 (s, 3H), 2.45 (s, 1H), 2.85 (m, 2H), 4.15 (m, 2H), 6.70 (m, 1H), 7.20 (m, 1H), 7.40 (m, 1H), 7.55 (m, 1H), 7.70 (m, 2H), 7.80 (m, 1H), 7.95 (m, 1H); Mass Spectrum: M+H+ 395.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07786115B2
Source datasetuspto-grants-2010_08
ORD IDord-7097e5ada7994541b30f95132dd944a1
Source noteuspto-grants-2010_08