Water → 3-Cyclopentyloxy-2-nitro-5-phenoxy-pyridine

HRID 1966221Notes

Reaction equation

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

Participants

Conditions

Temperature: 100 °C

Procedure

5-Chloro-3-cyclopentyloxy-2-nitro-pyridine (0.8 mmol) is dissolved in DMF (8 ml), phenol (3 eq.) and K2CO3 (4 eq.) is added. The reaction mixture is heated to 100° C. in the microwave for 60 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-Cyclopentyloxy-2-nitro-5-phenoxy-pyridine is obtained after column chromatography (heptane/ethyl acetate) as yellow oil in a yield of 60%; HPLC (method C): 2.23 min; LC-MS (method A): 2.31 min, 301.15 (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-678021e8d8fc4119ae14fb12c019b025
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08420642B2

Reaction notes

Loading…