Water → 5-(4-Methanesulfonyl-phenoxy)-3-(2-methoxy-ethoxy)-pyridine-2-ylamine

HRID 1966254Notes

Reaction equation

HRID 1966254 reaction equation
[CH3:1][S:2]([C:5]1[CH:25]=[CH:24][C:8]([O:9][C:10]2[CH:11]=[C:12]([O:19][CH2:20][CH2:21][O:22][CH3:23])[C:13]([N+:16]([O-])=O)=[N:14][CH:15]=2)=[CH:7][CH:6]=1)(=[O:4])=[O:3].O>C(O)(=O)C.[Zn]>[CH3:1][S:2]([C:5]1[CH:25]=[CH:24][C:8]([O:9][C:10]2[CH:11]=[C:12]([O:19][CH2:20][CH2:21][O:22][CH3:23])[C:13]([NH2:16])=[N:14][CH:15]=2)=[CH:7][CH:6]=1)(=[O:4])=[O:3]

Participants

5

Reactant 2

HCID 962WaterHCID 674867165-(4-Methanesulfonyl-phenoxy)-3-(2-methoxy-ethoxy)-2-nitro-pyridine

Product 1

HCID 674864395-(4-Methanesulfonyl-phenoxy)-3-(2-methoxy-ethoxy)-pyridine-2-ylamineYield 96%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
105 °C

Procedure

5-(4-Methanesulfonyl-phenoxy)-3-(2-methoxy-ethoxy)-2-nitro-pyridine (0.39 mmol) is dissolved in acetic acid (4 ml). After addition of water (1.2 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. 5-(4-Methanesulfonyl-phenoxy)-3-(2-methoxy-ethoxy)-pyridine-2-ylamine is obtained as yellow oil in a yield of 96%. HPLC (method C): 1.21 min, LC-MS (method A): 0.55 min, 339.15 (MO.

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-3fac03becb1543a99a8cbd4027961343
Source dataset
uspto-grants-2013_04
Patent number
US08420642B2

Reaction notes

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