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3- Nitro-4-aminoanisole

The 3-nitro-4-aminoanisole was the technical commercial product, m.p. 124-126°, obtained from E. I. du Pont de Nemours and Company. [Pg.50]

Nitro-4-aminoanisole (16.8 g., 0.10 mole) [Org. Syntheses, 25, 78 (1945) ] is added to a solution of 30 ml. of concentrated sulfuric acid and 100 ml. of water, and the resulting mixture is cooled to 0-5°. A solution of 7 g. (0.102 mole) of sodium nitrite in 20 ml. of water is added slowly at this temperature, and the mixture is allowed to stand for 2 hours at 0-5°. After filtration to remove a small amount of 3-nitro-4-aminoanisole, the filtrate is added dropwise to a boiling mixture of 100 ml. of water, 6.4 g. of copper sulfate, 15.6 g. of sodium bromide, and 2 g. of copper powder. After another 30-minute boiling, the mixture is cooled and extracted with ether. The ethereal extracts are washed with water, dried over calcium chloride, and distilled. 3-Nitro-4-bromoanisole boils at 153-154°/13 mm. and is obtained in a 75% yield (17.5 g.). [Pg.225]

Melhoxy-8-nitroqulnollne (3).2 A mixture ot 3-nitro-4-aminoanisole 1 (33.6 g, 0 2 mol), arsenic acid (56.8 g, 0.4 mol) in 85% H3PO4 was heated to 100°C and acrolein 2 (15.94 g, 0.284 mol) was added dropwise under stirring. After aA ot 2 was added (25-30 min), the mixture was maintained for an additional 30 min at the same temperature. The solution was poured into water (800 ml.), decolorized with charcoal and made alkaline with NH4OH. The precipitate after filtration and recrystallization from EtOAc (600 ml) gave 25 g ot 3 (60%), mp 157-158 C. [Pg.179]

N 21-54% orn-colored ndls + % H2O (from dil ale), mp - explodes violently at 169-72° readily sol in glacial acet ac, chlf 8c ethyl acet sol in warm alkalies, giving a blue-red soln si sol in acet 8c benz was prepd by diazotizing either 5-nitro-3-amino be nzopyro-catechol-l-methyl ether or 2-bromo-5-nitro-3-aminoanisole (Refs 1, 2 Sc 3)... [Pg.67]

Nitro-4-diazore orcinol-3-methyl ether [called 6-Nitro-4 diazo-resorcin-3 methylather or 5-Nitro-2-methoxy-p-chinon-diazid-(l) in Ger], C7H5N3O4 mw 195.13, N 21.54% yel ndls or flakes, mp - explodes at 178 was prepd by diazotizing 4,5-dinitro-2-aminoanisole... [Pg.68]

Dinitro-3,3 -dimetboxyazoxybenzene, mp between 170 200 was formed in small quantity by the reduction of 3,5-dinitroanisole with Na2S2 in ale, in addn to a larger quantity of 5 nitro-3-aminoanisole Refs l)BerI 16, 636 2)j,j.Bianksnia,... [Pg.666]

Other functional groups may be present during reduction. Aromatic amino ethers are prepared by the same general procedures described above, e.g., 772-aminoanisole (80%) and 2-aminodiphenyl ether (94%). The reduction of o-nitrobenzaldehyde to the sensitive o-aminobenzaldehyde is successfully accomplished by the action of ferrous sulfate and ammonia (75%). m-Dimethylaminobenzaldehyde is formed by reduction of the nitro acetal in aqueous solution with sodium sulfide followed by methyla-tion (74% over-all) or by catalytic reduction of m-nitrobenzaldehyde in... [Pg.333]


See other pages where 3- Nitro-4-aminoanisole is mentioned: [Pg.48]    [Pg.50]    [Pg.51]    [Pg.25]    [Pg.26]    [Pg.89]    [Pg.1020]    [Pg.306]    [Pg.1020]    [Pg.48]    [Pg.50]    [Pg.51]    [Pg.25]    [Pg.26]    [Pg.89]    [Pg.351]    [Pg.1020]    [Pg.352]    [Pg.306]    [Pg.361]    [Pg.1020]    [Pg.204]   
See also in sourсe #XX -- [ Pg.27 , Pg.48 ]

See also in sourсe #XX -- [ Pg.1020 ]

See also in sourсe #XX -- [ Pg.1020 ]




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3-Nitro-4-aminoanisole, diazotization

Aminoanisole

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