Acetic Acid → 3-(2-Methoxyethoxy)-5-phenoxy-pyridine-2-ylamine

HRID 1966222Notes

Reaction equation

HRID 1966222 reaction equation
[CH:1]1([O:6][C:7]2[C:8]([N+:20]([O-])=O)=[N:9][CH:10]=[C:11]([O:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH:12]=2)[CH2:5]CCC1.O.[C:24](O)(=[O:26])C>[Zn]>[CH3:24][O:26][CH2:5][CH2:1][O:6][C:7]1[C:8]([NH2:20])=[N:9][CH:10]=[C:11]([O:13][C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:12]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 962WaterHCID 674865893-Cyclopentyloxy-2-nitro-5-phenoxy-pyridine

Product 1

HCID 674861883-(2-Methoxyethoxy)-5-phenoxy-pyridine-2-ylamineYield 72%

Reagents, catalysts & solvents 1

HCID 23994ZincCatalyst

Conditions

Temperature
100 °C

Procedure

3-Cyclopentyloxy-2-nitro-5-phenoxy-pyridine (0.46 mmol) is dissolved in acetic acid (1.5 ml). After addition of water (1.5 ml), zinc powder (6.2 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 washed 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 72%; HPLC (method C): 1.43 min; LC-MS (method A): 1.231 min, 271.15 (M+H+).

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-a37fb655d8d8429db1c16c60bc2560ff
Source dataset
uspto-grants-2013_04
Patent number
US08420642B2

Reaction notes

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