4- Methoxy-2-nitroaniline

Using 2-methoxy-4-nitroaniline as diazo component instead and coupling onto the same bifunctional coupling component yields Pigment Yellow 198 ... 

The photohydrolysis of 2-fluoro-4-nitroanisole to 2-methoxy-5-nitrophenole is sensitized by benzophenone and completely quenched by sodium sorbate The excited state multiplicity in photoaminations has also been studied. Photolysis of mNA in liquid ammonia yields m-nitroaniline. If the amination is carried out in a large excess of benzophenone, 2-methoxy-4-nitroaniline is formed instead and thus an excited singlet state as reacting species is envisaged in the unsensitized photoamination loo.ioi). it may well be that uptake of the nucleophile present in high concentration successfully competes with intersystem crossing. 

With m-nitroanisole in liquid ammonia the benzophenone-sensitized reaction yields inter alia 2-methoxy-4-nitroaniline as a product and no m-nitroaniline, which is formed in very high yield upon direct irradiation in liquid ammonia as well as in NH3/CH3OH. In the latter instance l/4> varies linearly with 1/[NH3], suggesting that the reaction is either singlet or triplet but not of a mixed type. 

Table 3 shows that the fluoroarene yield increases with the irradiation power and is dependent again on the hydrogen fluoride/pyridine ratio (cf. 2-methoxy-4-nitroaniline). An optimum ratio must, most probably, be determined for each substrate. It should also be noted that photochemical fluorodediazoniation does not occur in pure hydrogen fluoride. This observation probably implies that not only light is involved in the weakening of the C-N bond. On the other hand, benzene is formed together with fluorobenzene when pyridine is replaced by 2,4,6-trimethylpyridine such a phenomenon is consistent with the occurrence of aryl radicals."... 

Primary aromatic amines can be converted into the corresponding hydroxy compounds in various ways. In some cases this can be done by use of dilute acid or alkali under specific conditions, but that method is used mainly in industry and is rarely suitable for laboratory practice. 4-Amino-2,7- and -2,6-naphthalenedisulfonic acid and 8-amino-1,6-naphthalenedisulfonic acid are converted quantitatively into the corresponding hydroxynaphthalenedisulfonic acids when their acid salts are heated in water at 180° 555 and 2-methoxy-4-nitroaniline affords 4-nitroguaiacol in 86% yield when boiled for 30 hours with aqueous sodium hydroxide.556... 

Methoxy-4-nitroaniline 2-Methoxy-5-nitroaniline 4-Methoxy-2 nitroaniline 2-Methoxyphenol... 

Synthesis started with the reaction of commercially available 2-methoxy-4-nitroaniline, 1, with potassium hydroxide in aqueous dimethylsulfoxide to yield a phenol (2). The phenol was alkylated with dibromotetrafluoroethane following the general route described by Rico and Waskselman to give 2 (8). The addition of a catalytic amount of propanethiol is required for this reaction to proceed since it assists in the in-situ generation of tetrafluoroethylene, the electrophile in the reaction. 

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