Acetic Acid → 3-(2-Methoxy-ethoxy)-5-(pyridine-3-yloxy)-pyridine-2-ylamine

HRID 1966250Notes

Reaction equation

[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[C:7]([N+:19]([O-])=O)=[N:8][CH:9]=[C:10]([O:12][C:13]2[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=2)[CH:11]=1.C(O)(=O)C>[Zn].O>[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[C:7]([NH2:19])=[N:8][CH:9]=[C:10]([O:12][C:13]2[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=2)[CH:11]=1

Participants

Conditions

Temperature: 105 °C

Procedure

3-(2-Methoxy-ethoxy)-2-nitro-5-(pyridine-3-yloxy)-pyridine (0.52 mmol) is dissolved in acetic acid (50 eq.). After addition of water (1.5 ml), zinc powder (6.3 eq.) is added and the reaction suspension is heated to 105° C. for 90 minutes. The reaction suspension is cooled to room temperature and filtrated. The filtrate is pored into 3.5% NaOH (30 ml) and extracted with dichloromethane. The combined organic layers are washed with brine, dried over MgSO4 and the solvent is removed in vacuo. 3-(2-Methoxy-ethoxy)-5-(pyridine-3-yloxy)-pyridine-2-ylamine is obtained as yellow oil in a yield of 93%. HPLC (method C): 0.44 min, LC-MS (method A): 0.46 min, 262.15 (MH+),

Workup

additionis added
temperatureThe reaction suspension is cooled to room temperature
filtrationfiltrated
extractionextracted with dichloromethane
washThe combined organic layers are washed with brine
dry with materialdried over MgSO4
customthe solvent is removed in vacuo

Sources & evidence

ORD record: ord-fe35f568e28c42bea212f73572d44663
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08420642B2

Reaction notes

Loading…