1,3-BENZODIOXOL-4-AMINE

The Boc starting material G2 (257 mg; 1.08 MMOL) was dissolved in 4M HCI/DIOXANE (5.0 mL) and stirred at room temperature for 1 hr. The solvent was evaporated and the residue diluted with saturated sodium bicarbonate (few mL) and 1 M NAOH (1 ML), extracted with EtOAc (2x), dried (MGS04), filtered and evaporated to dryness to provide the crude 2, 3-methylene DIOXYANILINE G3 (158 mg; 106percent).[d][1 , 3]dioxol-4-amine To a solution of 4-nitrobenzo[d][1 , 3]dioxoie (2.0 g, 12 mmol) in ethanol (80 mL) was added Raney Ni (ca. 0.5 g). The mixture was stirred under an atmosphere of hydrogen for 4 hours. The catalyst was removed by filtration and the filtrate was concentrated. The residue was purified by silica gel chromatography (dich.oromethane) to afford the product benzo[d][1.3]dioxol-4-amine (1 .04 g, yield 63 percent). H NMR (400 MHz, CDCITo a stirring solution of General procedure: 6-Bromo-4-chloroquinoline (1.0 equiv.) and 3, 4, 5-trimethoxyaniline (1.1 equiv.) were suspended in ethanol (10 mL) and refluxed for 18 h. The crude mixture was purified by flash chromatography using EtOAc:hexane followed by 1-5% methanol in EtOAc, solvent was removed under reduced pressure to afford the desired product (1, 8-11, 13-31, and 33-43).

Molecular Weight:137.14
XLogP3:1.1
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Exact Mass:137.047678466
Monoisotopic Mass:137.047678466
Topological Polar Surface Area:44.5
Heavy Atom Count:10
Complexity:129
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes