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

HRID 1966250
Notes
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Reaction equation

HRID 1966250 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 674864173-(2-Methoxy-ethoxy)-2-nitro-5-(pyridine-3-yloxy)-pyridine

Product 1

HCID 674865053-(2-Methoxy-ethoxy)-5-(pyridine-3-yloxy)-pyridine-2-ylamineYield 93%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 962WaterSolvent

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

  1. additionis added
  2. temperatureThe reaction suspension is cooled to room temperature
  3. filtrationfiltrated
  4. extractionextracted with dichloromethane
  5. washThe combined organic layers are washed with brine
  6. dry with materialdried over MgSO4
  7. 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

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes