N,N-Dimethyl-2-nitrobenzenamine

(a) V, V-dimethylbenzene-l, 2-diamine. To a hydrogenation reaction flask was added iV, iV-dimethyl-2-nitrobenzenamine (1.00 g, 6.02 mmol), EtOH (22 niL) and EtOAc (60 mL). To the resulting orange solution was added Pd/C (5%, 0.67 g) and then the black suspension was degassed three times and filled with H2(g) (50 psi). The black suspension was shaken at room temperature for 5h, filtered through celite (2 in h x 1.5 in w), washed with additional EtOAc (50 mL) and concentrated to an orange residue. Purification by flash column chromatography (silica gel, with EtOAc :Hexanes, 1:15) gave 0.73 g (89%) of the title compound as an orange oil: 1H-NMR (CDCl3): 7.00 (dd, J= 7.8 and 1.5 Hz, IH), 6.90 (td, J = 7.6 and 1.5 Hz, IH), 6.76-6.68 (m, 2H), 3.93 (br s, 2H), 2.65 (s, 6H).(b) N-(2-Dimethylaminophenyl)-9-oxo-9#-fluorene-l- carboxamide. The title compound was prepared in a manner similar to Example 9. From (0.281 g, 2.06 mmol) and 9-oxo-9H-fluorene-l-carbonyl chloride (0.500 g, 2.06 mmol) was obtained 0.356 g (50%) of the title compound as a brown solid: mp 152-1530C; 1H-NMR (CDCl3): 10.77 (br s, IH), 8.42-8.40 (m, IH), 8.06 (d, J = 8.2 Hz, IH), 7.72-7.54 (m, 5H), 7.36-7.33 (m, IH), 7.18-7.12 (m, 3H), 2.70 (s, 6H).Step 2) Preparation of 2-(N, N-Dimethylamino)-aniline To a stirred solution of the product of step 1 (0.415 g, 2.50 mmol) in 2:1 methanol/acetic acid (10 ml) was added iron filings (0.420 mg, 7.52 mmol). The mixture was heated to reflux. After 2 hours the reaction mixture was filtered thru Celite. The filter cake was washed with ethyl acetate and the filtrate was then extracted with ethyl acetate. The combined organic layers were washed with aqueous sodium bicarbonate solution and brine, dried (sodium sulfate) and concentrated. The resulting residue was purified by flash chromatography over silica (hexanes/ethyl acetate) to afford 0.208 g (61%) of product as an amber oil: 1H NMR (CDCl3) delta 7.07 (d, 1H), 6.96 (t, 1H), 6.79 (m, 2H), 4.09 (br s, 2H), 2.73 (s, 6H) ppm.(ii) N, N-dimethyl-2-nitroaniline (4.99 g, 30 mmol) was hydrogenated at 1 atmosphere hydrogen over 10% palladium on carbon paste (0.64 g, 3.0 mmol) in ethanol (100 ml) for 48 hours. The catalyst was filtered off and the filtrate concentrated in vacuo to yield N, N-dimethyl-1 , 2-benzenediamine (3.89 g) as an oil.

Molecular Weight:166.18
XLogP3:1.9
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:1
Exact Mass:166.074227566
Monoisotopic Mass:166.074227566
Topological Polar Surface Area:49.1
Heavy Atom Count:12
Complexity:165
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes