Acetic Acid → 5-(2-Nitro-ethyl)-2-phenoxy-pyridine

HRID 1694245

Reaction equation

HRID 1694245 reaction equation
[N+:1](/[CH:4]=[CH:5]/[C:6]1[CH:7]=[CH:8][C:9]([O:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[N:10][CH:11]=1)([O-:3])=[O:2].C(O)(=O)C.[B-].[Na+].O>CS(C)=O>[N+:1]([CH2:4][CH2:5][C:6]1[CH:7]=[CH:8][C:9]([O:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[N:10][CH:11]=1)([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 22959485VertellusHCID 592552955-((E)-2-Nitro-vinyl)-2-phenoxy-pyridine

Product 1

HCID 576263415-(2-Nitro-ethyl)-2-phenoxy-pyridine

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 5-((E)-2-nitro-vinyl)-2-phenoxy-pyridine described in Manufacturing Example 232-1-3 (5.97 g, 24.6 mmol) and acetic acid (3.2 mL) in dimethyl sulfoxide (52 mL) was added sodium borohydrate (1.4 g, 36.9 mmol), at room temperature while cooling appropriately. This mixture was stirred for 30 minutes at room temperature. This mixture was cooled appropriately, then, water was added, which was stirred for 30 minutes at room temperature. This mixture was liquid-separated, and the organic layer was separated. The organic layer was washed with water, dried over anhydrous magnesium sulfate, and then filtered. The filtrate was concentrated under a reduced pressure to obtain the title compound (5.72 g) as a crude product.

Workup

  1. temperatureThis mixture was cooled appropriately
  2. stirringwhich was stirred for 30 minutes at room temperature
  3. customThis mixture was liquid-separated
  4. customthe organic layer was separated
  5. washThe organic layer was washed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated under a reduced pressure

Sources & evidence

ORD record
ord-b2bf1258499d4b7a90fb5efd6c2d5814
Source dataset
uspto-grants-2012_04
Patent number
US08158657B2

Linked notes

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