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Hurlock, Ronald James (1958) A study of the preparation and properties of some nitropyrazoles. Doctoral thesis, Northern Polytechnic.
1. Nitration of 1-phenylpyrazole with mixed acids produces 1-p-nitrophenylpyrazole at 12°, 4-nitro-1-p-nitrophenylpyrazole at 22°, and 1-(2:4-dinitrophenyl)-4-nitropyrazole at 100°. The orientations of these compounds have been proved by synthesis.
2. Nitropyrazoles have been converted into di- and trinitro-compounds which have been orientated by synthesis.
3. The reaction between sodium nitromalonaldehyde monohydrate and phenylhydrazine hydrochloride to give 4-nitro-1-phenylpyrazole has been studied. This reaction has been extended to include the use of nitrophenylhydrazines to give 4-nitro-l-nitro- phenylpyrazoles.
4. 1-Phenylpyrazole and nitrophenylpyrazoles have been prepared by the reaction between 1:1:3:3-tetra- ethoxypropane and the appropriate phenylhydrazine hydrochloride.
5. 4-Nitropyrazoles and nitrophenylpyrazoles have been reduced to the corresponding amines by means of hydrazine hydrate and palladised charcoal.
6. 4-Amino-l-phenylpyrazole has been converted by means of the Skraup reaction into 1'-phenylpyrazolo- (4’:5’-2:3)pyridine the structure of which has been proved by synthesis and by ultra-violet absorption spectroscopy. Some pyrazolylquinolines have also been prepared from 1-aminophenylpyrazoles by means of the Skraup reaction.
7. The following new compounds have been prepared and characterised:
1-o-Nitrophenylpyrazole,
4-Nitro-1-o-nitrophenylpyrazole,
4-Nitro-1-m-nitrophenylpyrazole,
4-Nitro-1-p-nitrophenylpyrazole,
1-(2:4-Dinitrophenyl)-4-nitropyrazole,
1-(3:4-Dinitrophenyl)-4-nitropyrazole,
1-p-Aminophenyl-4-nitropyrazole,
1-p-Acetamidophenyl-4-nitropyrazole,
1-(4-Amino-3-nitrophenyl)-4-nitropyrazole,
1-(4-Acetamido-3-nitrophenyl)-4-nitropyrazole,
3-Methyl-4-nitro-1-p-nitrophenylpyrazole,
5-Methyl-4-nitro-1-p-nitrophenylpyrazole,
1-p-Aminophenyl-3-methyl-4-nitropyrazole,
1-p-Aminophenyl-5-methyl-4-nitropyrazole,
3-Methyl-4-nitro-1-phenylpyrazole,
5-Methyl-4-nitro-1-phenylpyrazole,
4-Amino-3-methyl-1-phenylpyrazole,
4-Amino-5-methyl-1-phenylpyrazole,
Ethyl 3-methyl-1-phenylpyrazole-5-carboxylate,
1'-Phenylpyrazolo(4':5´-2:3)pyridine,
3'-Methyl-1'-phenylpyrazolo(4’:5’-2:3)pyridine,
6-(1-pyrazolyl)quinoline,
6-(4-Nitro-1-pyrazolyl)quinoline.
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