2,6-DIMETHOXYANILINE

Off-white solid

To a solution of 78 (170 mg, 0.93 mmol) in AcOH (5 mL), EtOH (5 mL) and HIn a 150-ml autoclave, 2, 6-dimethoxynitrobenzene (10 g, 55 mmol) was added in that order, 30ml absolute ethanol, 0.2 g of 10percent Pd / C catalyst, Into high purity hydrogen to 1.0MPa, Reaction at room temperature.When the hydrogen pressure gauge is not falling as the end of the reaction.Filtration, the filtrate spin dry, A white solid 6.7g, 80percent yield.To conc. hydrochloric acid (15 mL) was added dihydrated tin chloride (69.6 g, 308 mmol) at rt. In another flask, compound 50 (5.6 g, 30.6 mmol) was solubilized in ethyl ether (60 mL). The resulting mixture was added by small portions to dissolved tin chloride in hydrochloric acid. The reaction was run to completion over 12 hours at rt. The mixture was then poured into cold water and basified to pH = 9 with aqueous sodium hydroxide and stirred at rt for 3 hours. The final suspension was filtered on Celite.(R).. After dilution of the filtrate with ethyl acetate and washing with water, the organic layer was dried over MgSOTo a mixture of N-hydroxy-2, 6-dimethoxybenzamide (1a) (0.237 g, 1.2 mmol), KGeneral procedure: Reactions facilitated by sonication were performed on a 1.0 mmol scale. Arylboronic acid 3 (1.0 equiv) and MeCN (5.0 mL) were added to a 25 mL microwave vial equipped with a stir bar, followed by HSA (1.5 equiv) and aq 1 M NaOH (5 equiv). The mixture was capped and set to stir for 5 min, then placed in an ultrasonic cleaner for 30 min (35 kHz, 90 W), at which time the vial was removed and a small aliquot was taken for reaction monitoring via HPLC analysis. The mixture was then placed back in the sonication bath for 30 min. This process was repeated until the reaction had gone to completion, or the reaction failed to progress, as monitored by HPLC. The reaction mixture was diluted with H2O (30 mL) and extracted with EtOAc (2 × 30mL). The combined organic extracts were dried (Na2SO4) and concentrated in vacuo. The residue was purified by flash chromatography (EtOAc/hexanes) to afford the desired amine product 2.

Molecular Weight:153.18
XLogP3:0.8
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:2
Exact Mass:153.078978594
Monoisotopic Mass:153.078978594
Topological Polar Surface Area:44.5
Heavy Atom Count:11
Complexity:107
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes