3-Hydroxypyridine → 3-(2-Methoxy-ethoxy)-2-nitro-5-(pyridine-3-yloxy)-pyridine

HRID 1966249Notes

Reaction equation

Cl[C:2]1[CH:3]=[C:4]([O:11][CH2:12][CH2:13][O:14][CH3:15])[C:5]([N+:8]([O-:10])=[O:9])=[N:6][CH:7]=1.[OH:16][C:17]1[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH3:15][O:14][CH2:13][CH2:12][O:11][C:4]1[C:5]([N+:8]([O-:10])=[O:9])=[N:6][CH:7]=[C:2]([O:16][C:17]2[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=2)[CH:3]=1

Participants

Conditions

Temperature: 120 °C

Procedure

5-Chloro-3-(2-methoxy-ethoxy)-2-nitro-pyridine (2.6 mmol) is dissolved in DMF (12 ml), 3-hydroxypyridine (3 eq.) and K2CO3 (4 eq.) is added. The reaction is heated to 120° C. in the microwave for 45 min. The solvent is removed in vacuo and dissolved in water (200 ml) and extracted with methyl-tert.-butyl ether. The combined organic layers are washed with brine, dried over MgSO4 and the solvent is removed in vacuo. 3-(2-Methoxy-ethoxy)-2-nitro-5-(pyridine-3-yloxy)-pyridine is obtained after column chromatography (heptane/ethyl acetate) as yellow oil in a yield of 20%. HPLC (method C): 1.23 min; LC-MS (method A): 1.18 min, 292.15 (MH+).

Workup

customThe solvent is removed in vacuo
dissolutiondissolved in water (200 ml)
extractionextracted with methyl-tert.-butyl ether
washThe combined organic layers are washed with brine
dry with materialdried over MgSO4
customthe solvent is removed in vacuo

Sources & evidence

ORD record: ord-d944f2dd455a444b8588c23b91e8146d
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08420642B2

Reaction notes

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