Hydrogen iodide → 2-(3,5-Dichloro-pyridin-4-yl)-1-(2,3-dihydroxy-4-methoxy-phenyl)-ethanone

HRID 1686088Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:23])[C:7]=1[CH2:8][C:9]([C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[C:13]([O:19]C)[C:12]=1[O:21]C)=[O:10].I>CC(O)=O>[Cl:23][C:6]1[CH:5]=[N:4][CH:3]=[C:2]([Cl:1])[C:7]=1[CH2:8][C:9]([C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[C:13]([OH:19])[C:12]=1[OH:21])=[O:10]

Participants

Conditions

Temperature: 80 °C

Procedure

2-(3,5-Dichloro-pyridin-4-yl)-1-(2,3,4-trimethoxy-phenyl)-ethanone from preparation 2 (1.25 g, 3.5 mmol) was dissolved in AcOH (100%, 9.25 mL) under argon. HI (55-58%, 4.55 mL) was added and the reaction mixture was heated at 80° C. for 18 hours. The reaction mixture was cooled to rt and evaporated in vacuo. NaHCO3 (sat., 150 mL) was added slowly followed by NaCl (sat., 50 mL). The organic products were extracted with EtOAc (4×100 mL). The combined organic phases were washed twice with NaCl (sat, 100 mL), Na2S2O3 (10%, 100 mL), dried over Na2SO4 and evaporated in vacuo. 2-(3,5-Dichloro-pyridin-4-yl)-1-(2,3-dihydroxy-4-methoxy-phenyl)-ethanone was obtained as a brown solid. 1H NMR (CDCl3) δ=11.88 (1H, s), 8.54 (2H, s), 7.51 (1H, d), 6.60 (1H, d), 5.62 (1H, bs), 4.67 (2H, s), 4.00 (3H, s). Yield 0.935 g (81%)

Workup

temperatureThe reaction mixture was cooled to rt
customevaporated in vacuo
additionNaHCO3 (sat., 150 mL) was added slowly
extractionThe organic products were extracted with EtOAc (4×100 mL)
washThe combined organic phases were washed twice with NaCl (sat, 100 mL), Na2S2O3 (10%, 100 mL)
dry with materialdried over Na2SO4
customevaporated in vacuo

Sources & evidence

ORD record: ord-06b5ae5ed3094820a76fdfef42958951
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08148537B2

Reaction notes

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