Water → 3-(2-Methoxy-1-methyl-ethoxy)-2-nitro-5-phenoxy-pyridine

HRID 1966238Notes

Reaction equation

Cl[C:2]1[CH:3]=[C:4]([O:11][CH:12]([CH3:16])[CH2:13][O:14][CH3:15])[C:5]([N+:8]([O-:10])=[O:9])=[N:6][CH:7]=1.[C:17]1([OH:23])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C>[CH3:15][O:14][CH2:13][CH:12]([CH3:16])[O:11][C:4]1[C:5]([N+:8]([O-:10])=[O:9])=[N:6][CH:7]=[C:2]([O:23][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:3]=1

Participants

Conditions

Temperature: 100 °C

Procedure

5-Chloro-3-(2-methoxy-1-methyl-ethoxy)-2-nitro-pyridine (2 mmol) is dissolved in DMF (15 ml), phenol (3 eq.) and K2CO3 (4 eq.) is added. The reaction is heated to 100° C. in the microwave for 45 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-1-methyl-ethoxy)-2-nitro-5-phenoxy-pyridine is obtained after column chromatography (heptane/ethyl acetate) as yellow oil in a yield of 22%. HPLC (method C): 2.03 min; LC-MS (method A): 1.99 min, 305.15 (MH+).

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-690ef0d3ed01416eac1efc9418569b9e
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08420642B2

Reaction notes

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