Iodine → N-[2-(3-Iodo-7-methoxy-1-naphthyl)ethyl]acetamide

HRID 1856905Notes

Reaction equation

S(=O)(=O)(O)O.[CH3:6][O:7][C:8]1[CH:17]=[C:16]2[C:11]([CH:12]=[CH:13][CH:14]=[C:15]2[CH2:18][CH2:19][NH:20][C:21](=[O:23])[CH3:22])=[CH:10][CH:9]=1.[I:24]I.I>O.C(O)(=O)C>[I:24][C:13]1[CH:14]=[C:15]([CH2:18][CH2:19][NH:20][C:21](=[O:23])[CH3:22])[C:16]2[C:11]([CH:12]=1)=[CH:10][CH:9]=[C:8]([O:7][CH3:6])[CH:17]=2

Participants

Conditions

Temperature: 65 °C

Procedure

A solution is formed by adding 46.25 ml of glacial acetic acid and 1.25 ml of concentrated sulphuric acid to 2.5 ml of water. 2.5 g of N-[2-(7-methoxy-1-naphthyl)ethyl]acetamide (10.31 mmol) are dissolved in 30 ml of that solution. 2.09 g of iodine (8.25 mmol) and 0.91 g of HIO3 (5.16 mmol) are then added to the reaction mixture, causing a grey precipitate to appear in a solution that has turned red. The reaction mixture is heated for 15 hours at 65° C., 5.14 ml of concentrated hydriodic acid (13.41 mmol) are added and heating is continued for 2 hours. The suspension is then poured into 200 ml of water and the precipitate that forms is filtered off. The precipitate is dissolved in ethyl acetate and washed with 1M NaHCO3, the organic phase is then concentrated, and purified by chromatography on silica gel, using a dichloromethane/methanol mixture, 99.5/0.5, as eluant, to yield the title product.

Workup

customA solution is formed
temperatureheating
filtrationthe precipitate that forms is filtered off
dissolutionThe precipitate is dissolved in ethyl acetate
washwashed with 1M NaHCO3
concentrationthe organic phase is then concentrated
custompurified by chromatography on silica gel

Sources & evidence

ORD record: ord-1a4be8483b224d8fbe142c3b128bf815
Source dataset: uspto-grants-2000_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06143789

Reaction notes

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