4-Chloro-N-ethylbenzenamine → HCID 58732800, compound

Participants

Reaction Steps

To a solution of N-ethyl-4-chloroaniline (650 mg, 4.18 mmol) in anhydrous toluene at 10° C. was slowly added a 2M solution of trimethylaluminium in hexanes (2.1 mL, 4.18 mmol). The reaction mixture was stirred at room temperature until gas evolution stopped. A second round bottom flask was charged with cis-2-methyl-1-(pyridine-4-carbonyl)-1,2,3,4-tetrahydro-quinoline-4-carboxylic acid methyl ester (370 mg, 1.19 mmol) and the preformed aluminum amide was added. The resulting reaction mixture was refluxed for 20 hours. The reaction was concentrated, quenched with 1M aqueous hydrochloric acid at 0° C. (exothermic!), basified with 1M aqueous sodium hydroxide, and extracted with ethyl acetate. The resulting organic layer was separated, washed with brine, dried over magnesium sulfate, and filtered. The filtrate was concentrated in vacuo to afford an orange oil which was purified via flash chromatography (1% methanol/methylene chloride) followed by HPLC to provide (±)-trans-2-methyl-1-(pyridine-4-carbonyl)-1,2,3,4-tetrahydro-quinoline-4-carboxylic acid (4-chloro-phenyl)-ethyl-amide (11%). 1H-NMR (CDCl3) δ: 1.02-1.18 (m, 6H), 1.60-1.70 (m, 1H), 2.45-2.55 (m, 1H), 3.60-3.70 (m, 1H), 3.80 (q, 2H), 4.98-5.10 (m, 1H), 6.40 (d, 1H), 6.90 (m, 2H), 7.00 (t, 1H), 7.30 (m, 2H), 7.50 (d, 2H), 7.60 (d, 2H), 8.55 (d, 2H). MS m/z: 434/436 (M+1).

Provenance & Evidence