3-nitro-5,6,7,8-tetrahydroquinoline synthesis
- Product Name:3-nitro-5,6,7,8-tetrahydroquinoline
- CAS Number:84531-35-1
- Molecular formula:C9H10N2O2
- Molecular Weight:178.19
14150-94-8
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108-94-1
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Yield:84531-35-1 97%
Reaction Conditions:
with ammonium acetate in ethanol at 65; for 1 h;Microwave irradiation;
Steps:
TCRT; Typical Procedure
To a solution of the dinitropyridone 1 (50 mg, 0.25 mmol) in EtOH (5 mL), cyclohexanone 4a (26 μL, 0.25 mmol) and NH4OAc (289 mg, 3.75 mmol) were added, and the resultant mixture was heated at 65 °C on an oil bath for 24 h. After removal of the solvent, the residue was washed with benzene (3 × 10 mL) to afford 5,6,7,8-tetrahydro-3-nitroquinoline (5a; 42 mg, 0.24 mmol, 95%) as a yellow powder. The reactions of dinitropyridone 1 with other ketones 4b-g were performed in a similar way. When the reaction was conducted using microwave heating, the procedure was analogous.
References:
Le, Thi Song;Asahara, Haruyasu;Nishiwaki, Nagatoshi [Synthesis,2014,vol. 46,# 16,art. no. SS-2014-F0139-OP,p. 2175 - 2178]
