5-AMINO-2-HYDROXYBENZONITRILE synthesis
- Product Name:5-AMINO-2-HYDROXYBENZONITRILE
- CAS Number:67608-58-6
- Molecular formula:C7H6N2O
- Molecular Weight:134.14
39835-14-8
67608-58-6
The general procedure for the synthesis of 4-amino-2-hydroxybenzonitrile from 2-hydroxy-4-nitrobenzonitrile is as follows: 1. 5-Amino-2-chlorophenol was synthesized from 2-amino-5-nitrophenol by a two-step reaction: a) Formation of diazonium salt using NaNO2 and subsequent reaction with CuCl to produce 2-chloro-5-nitrophenol in 68% yield. b) Careful reduction of nitro with H2 (1 atm) in the presence of Adam's catalyst gave the final amine derivative in 57% yield. 2. Synthesis of 5-amino-2-ethyl/n-propyl/cyclopropyl phenol was carried out in four steps starting from the corresponding 2-ethyl/cyclopropyl/n-propyl amine: a) Nitration reaction with potassium nitrate in the presence of sulfuric acid to give the corresponding 5-nitro-2-alkylaniline. b) Reaction with NaNO2 followed by reaction with H2O at 80°C for 2 hours to produce the corresponding 5-nitro-2-alkylphenol derivatives. c) Finally, the corresponding amine derivatives were obtained by hydrogenation of the nitro group. 3. Synthesis of 2-methoxy-4-hydroxybenzyl cyanide: a) Obtained by hydrolysis of methyl ether of 2-methoxy-4-nitrobenzonitrile with LiCl. b) Subsequently, the nitro group was reduced with SnCl2-2H2O in the presence of 6N HCl.
39835-14-8
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67608-58-6
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Yield:67608-58-6 100%
Reaction Conditions:
with palladium 10% on activated carbon;hydrogen in ethanol at 20;
References:
No?l, Sabrina;Hoegy, Fran?oise;Rivault, Freddy;Rognan, Didier;Schalk, Isabelle J.;Mislin, Ga?tan L.A. [Bioorganic and Medicinal Chemistry Letters,2014,vol. 24,# 1,p. 132 - 135]
7251-09-4
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67608-58-6
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101084-96-2
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$23.00/1g
67608-58-6
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121-14-2
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$25.39/1.2mL
67608-58-6
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3236-33-7
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67608-58-6
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