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

HRID 456032Notes

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 it 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 it
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-691462be8bb54528b01311484a7a0e9d
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08497380B2

Reaction notes

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