* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Reference：
[1] Australian Journal of Chemistry, 1980, vol. 33, # 12, p. 2777 - 2779
2
[ 4837-88-1 ]
[ 75-65-0 ]
[ 77901-52-1 ]
Yield
Reaction Conditions
Operation in experiment
22%
With potassium permanganate In water for 4 h; Heating / reflux
To a suspension of 4a (2.0 g, 12 mmol) in tert-BuOH (10 mL) and water (20 mL) was added KMnO4 (5.7 g, 36 mmoL). The mixture was heated to reflux for 4 h. The cooled reaction mixture was filtered through diatomaceous earth. The filtrate was acidified using aqueous 12 N HCl solution and extracted twice with EtOAc. The combined organic layer was washed with water and brine, dried (MgSO4), filtered and concentrated under reduced pressure. The resulting residue was treated with excess diazomethane/Et2O solution to give ester 9a (548 mg, 22percent yield).
With potassium permanganate; In water; for 4.0h;Heating / reflux;
To a suspension of 4a (2.0 g, 12 mmol) in tert-BuOH (10 mL) and water (20 mL) was added KMnO4 (5.7 g, 36 mmoL). The mixture was heated to reflux for 4 h. The cooled reaction mixture was filtered through diatomaceous earth. The filtrate was acidified using aqueous 12 N HCl solution and extracted twice with EtOAc. The combined organic layer was washed with water and brine, dried (MgSO4), filtered and concentrated under reduced pressure. The resulting residue was treated with excess diazomethane/Et2O solution to give ester 9a (548 mg, 22% yield).
With hydrogen;palladium 10% on activated carbon; In methanol; for 1.0h;
A mixture of 9a (547 mg, 2.59 mmol) and 10% Pd/C (30 mg) in MeOH (25 mL) was stirred under hydrogen (1 atm.) for 1 h. The catalyst was removed by filtration through diatomaceous earth. The filtrate was concentrated under reduced pressure to give aniline 9b (443 mg, 94% yield).
With boron tribromide; In dichloromethane; at 20.0℃; for 1.0h;Cooling with ice;
Intermediate 1B8: 2-Amino-6-(difluoromethoxy)benzoic acida) Methyl 2-hydroxy-6-nitrobenzoateA yellow stirred solution of <strong>[77901-52-1]methyl 2-methoxy-6-nitrobenzoate</strong> (CAS registry 77901-52-1)(650 mg, 2.99 mmol) in DCM (15 ml) at 0C was dropwise treated with BBr3 (1 M in DCM)(12 mL, 11 .94 mmol). The resulting mixture was stirred for 1 h at rt. It was poured intocrushed ice, the organic layer was separated and the aqueous layer was extracted withEtOAc and dried over MgSO4, evaporated under reduced pressure to afford a black residue(750 mg).The crude product was purified by chromatography on silica gel (cyclohexaneEtOAc, 0% to 60% ) to provide the title compound as a red residue (0.250 g, 42% yield).HPLC RtM2= 0.75 mm ; ESIMS: 196 [(M-H)].1H NMR (400 MHz, DMSO-d6): O 10.99 Cs, 1 H), 7.63 (dd, 1 H), 7.53 Ct, 1 H), 7.33 (dd, 1H),3.81 Cs, 3H).
Chemistry
Pharmaceutical Intermediates
Inhibitors/Agonists
Material Science
For Research Only
110K+ Compounds
Competitive Price
1-2 Day Shipping
