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Step C.; A solution of sodium nitrite (0.67 g, 9.94 mmol) and H2O (2.06 mL) was added dropwise at 0 C. to a solution of 2-chloro-5-methylbenzenamine (1.2 g, 8.29 mmol) in 12N HCl (12.8 mL) and TFA (2.5 mL). The reaction mixture was stirred at 0 C. for 1 h followed by the dropwise addition of a solution of tin(II)chloride (3.5 g, 18.2 mmol) in 12N HCl (4.9 mL) and H2O (0.7 ml) at 0 C. The reaction mixture stirred for 15 h at 20 C. and was filtered to give 1-(2-chloro-5-methylphenyl)hydrazine hydrochloride as a white solid (0.84 g, 4.3 mmol).
6-Chloro-9-methyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole hydrochloride[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
Step D.; A solution of <strong>[922510-92-7]1-<strong>[922510-92-7](2-chloro-5-methylphenyl)hydrazine hydrochloride</strong></strong> (0.1 g, 0.52 mmol) and 4-piperidone hydrochloride monohydrate (79.6 mg, 0.52 mmol) in EtOH (1.5 mL) was stirred at 75 C. for 15 h. Following the addition of 12N HCl (0.13 mL, 1.6 mmol), the reaction was filtered and rinsed with cold EtOH to give the title compound (65.2 mg, 0.24 mmol): MS (ES) 221.1 (M+H).
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