Water → 3-(2-Methoxyethoxy)-5-phenoxy-pyridine-2-ylamine

HRID 1966217Notes

Reaction equation

HRID 1966217 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:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:11]=1.O>C(O)(=O)C.[Zn]>[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:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:11]=1

Participants

5

Reactant 2

HCID 962WaterHCID 674862083-(2-Methoxy-ethoxy)-2-nitro-5-phenoxy-pyridine

Product 1

HCID 674861883-(2-Methoxyethoxy)-5-phenoxy-pyridine-2-ylamineYield 76%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

3-(2-Methoxy-ethoxy)-2-nitro-5-phenoxy-pyridine (0.4 mmol) is dissolved in acetic acid (1.3 ml). After addition of water (1.3 ml), zinc powder (6 eq.) is added and the reaction suspension is heated to 100° C. for 3 h. 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 extracted with brine, dried over MgSO4 and the solvent is removed in vacuo. 3-(2-Methoxyethoxy)-5-phenoxy-pyridine-2-ylamine is obtained as brown oil in a yield of 76%. HPLC (method C): 1.43 min; LC-MS (method A): 0.808 min, 261.15 (M+H+).

Workup

  1. additionis added
  2. temperatureThe reaction suspension is cooled to room temperature
  3. filtrationfiltrated
  4. extractionextracted with dichloromethane
  5. extractionThe combined organic layers are extracted with brine
  6. dry with materialdried over MgSO4
  7. customthe solvent is removed in vacuo

Sources & evidence

ORD record
ord-1216b7698ca44bc2b316b41a4196a362
Source dataset
uspto-grants-2013_04
Patent number
US08420642B2

Reaction notes

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