Water → 3-(2-Methoxy-ethoxy)-2-nitro-5-phenoxy-pyridine

HRID 1966216Notes

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.[C:16]1([OH:22])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C([O-])([O-])=O.[K+].[K+].O>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:22][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:3]=1

Participants

Conditions

Temperature: 100 °C

Procedure

5-Chloro-3-(2-methoxy-ethoxy)-2-nitro-pyridine (0.68 mmol) is dissolved in DMF (7 ml), phenol (3 eq.) and K2CO3 (4 eq.) is added. The reaction mixture is heated to 100° C. in the microwave for 30 min. The reaction solution is pored into water 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-phenoxy-pyridine is obtained after column chromatography (heptane ethyl acetate) as yellow oil in a yield of 62%; HPLC (method C): 1.93 min; LC-MS (method A): 1.80 min, 291.15 (M+H+).

Workup

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-e5fade98a0524b7bbea007ce72821e70
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08420642B2

Reaction notes

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