5-Iodo-7-nitro-1-trifluoroacetyl-1,2,3,4-tetrahydroquinoline → 5-Chloro-7-nitro-1,2,3,4-tetrahydroquinoline

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Reaction Steps

A solution of 5-iodo-7-nitro-1-trifluoroacetyl-1,2,3,4-tetrahydroquinoline (D53P) (1.69 g, 6.73 mmol) in DMF (25 ml) was treated with copper (I) chloride (1.66 g, 16.8 mmol) at 130C. for 7 h. On cooling the solution was filtered and the filtrate concentrated in vacuo. The residue was dissolved in EtOAc and washed with 5M HCl, then dried over MgSO4 and concentrated in vacuo. The crude product was purified by column chromatography to give a (1:1) mixture of the title compound and 5-chloro-7-nitro-1-trifluoroacetyl-1,2,3,4-tetrahydroquinoline (591 mg). This mixture was treated with potassium carbonate in methanol to yield the title compound (450 mg) as a brown solid. 1H NMR (400 MHz, CDCl3) δ (ppm): 7.49 (d, 1H), 7.19 (d, 1H), 4.31 (br.s, 1H), 3.33 (m, 2H), 2.82 (t, 2H), 1.98 (m, 2H).

Provenance & Evidence