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ChemicalBook CAS DataBase List N,N-DIMETHYL-3-NITROANILINE
619-31-8

N,N-DIMETHYL-3-NITROANILINE synthesis

10synthesis methods
-

Yield: 86%

Reaction Conditions:

with sodium hydride in N,N-dimethyl-formamide;mineral oil at 0 - 20; for 4 h;

Steps:

37.1
Synthesis of 8-(Dimethylamino)-1,2,3,4-tetrahydrobenzo[h][1,6]naphthyridine-5(6H)-one hydrochloride Step 1: Synthesis of N,N-Dimethyl-3-nitroaniline [Show Image] 3-nitroaniline (1.0 g, 7.25 mmol) was dissolved in N,N-dimethylformamide (50 ml), added with sodium hydride (1.7 g, 21.7 mmol) and iodomethane (2.7 ml, 21.7 mmol) at 0 °C. The resulting mixture was stirred for 4 hours at room temperature and poured into ice water. The mixture was extracted with ethyl acetate, dried over anhydrous magnesium sulfate, and concentrated to dryness. The residue was then purified by flash column chromatography (hexane : ethyl acetate = 1 : 1) to obtain the title compound (2.0 g, yield:86%, yellow solid). 1H NMR(400MHz, CDCl3); δ 7.53-7.48(m, 1H), 7.33(t, J=8.0Hz, 1H), 6.96(d, J=8.0Hz, 1H), 3.04(s, 6H)

References:

Jeil Pharmaceutical Co., Ltd. EP2364983, 2011, A2 Location in patent:Page/Page column 51

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