1,2-Dichloroethane → N-(8-Phenyloctyl)-3-iodo-4-hydroxybenzamide

To a stirring solution of 3-iodo-4-hydroxy-benzoic acid (2.64 g, 10.00 mmol) in fresh DMF (50 mL) at ambient temperature under an atmosphere of N2 was added EDC (2.11 g, 11.00 mmol), HOBt (1.49 g, 11.00 mmol) and DIPEA (1.94 g, 2.61 mL, 15.00 mmol). The solution was allowed to stir at ambient temperature for 1 hour at which time 8-phenyl-octylamine (2.46 g, 2.39 mL, 12 mmol) was added at one time. The solution was allowed to stir for an additional 4 hours at which time the it was diluted with water (250 mL) and extracted with ethyl acetate (250 mL). The organic phase was washed with water (2×250 mL), saturated aqueous NaHCO3 (250 mL) and saturated aqueous NaCl (250 mL). The solvent was removed in vacuo to yield 4.62 g of crude oil. The crude oil was purified by column chromatography (7:3 hexane:ethyl acetate) to yield 4.47 g (99%) of the desired product as a clear oil, which crystallized upon standing. 1H NMR (CDCl3) δ 8.19 (dd, 2H), 7.60 (dd, 1H), 7.20 (m, 4H), 6.97 (dd, 1H), 6.32 (t, 1H), 3.39 (q, 2H), 2.57 (t, 2H), 1.58 (m, 4H), 1.30 (m, 8H).

1. additionwas added at one time
2. extractionextracted with ethyl acetate (250 mL)
3. washThe organic phase was washed with water (2×250 mL), saturated aqueous NaHCO3 (250 mL) and saturated aqueous NaCl (250 mL)
4. customThe solvent was removed in vacuo
5. customto yield 4.62 g of crude oil
6. customThe crude oil was purified by column chromatography (7:3 hexane:ethyl acetate)

ORD record

ord-d0544d0a7c374fe59fee4473db227609

Source dataset

uspto-grants-2002_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06451827B2