Acetic Acid → (E)-2-((4-(2-Nitrovinyl)benzyl)oxy)pyridine

HRID 557265Notes

Reaction equation

HRID 557265 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[O:7][CH2:8][C:9]1[CH:16]=[CH:15][C:12]([CH:13]=O)=[CH:11][CH:10]=1.[N+:17]([CH3:20])([O-:19])=[O:18].C([O-])(=O)C.[NH4+].C(O)(=O)C>O.C(OCC)(=O)C>[N+:17](/[CH:20]=[CH:13]/[C:12]1[CH:15]=[CH:16][C:9]([CH2:8][O:7][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=2)=[CH:10][CH:11]=1)([O-:19])=[O:18]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 6375NitromethaneHCID 517165Ammonium AcetateHCID 592551184-((Pyridin-2-yloxy)methyl)benzaldehyde

Product 1

HCID 58076258(E)-2-((4-(2-Nitrovinyl)benzyl)oxy)pyridine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 4-(pyridin-2-yloxymethyl)-benzaldehyde described in Preparation Example 1-4-2 (26.8 g, 126 mmol), nitro methane (34 mL, 630 mmol), ammonium acetate (19 g, 252 mmol) and acetic acid (90 mL) was stirred at 100° C for 90 minutes. To the reaction solution were added ethyl acetate and water to carry out liquid separation. The organic layer thereof was separated, washed with water (five times) and saturated sodium bicarbonate water (once), dried over anhydrous magnesium sulfate and then filtered. The filtrate thereof was concentrated under a reduced pressure to obtain the title compound (31 g) as a crude product.

Workup

  1. customliquid separation
  2. customThe organic layer thereof was separated
  3. washwashed with water (five times) and saturated sodium bicarbonate water (once),
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate thereof was concentrated under a reduced pressure

Sources & evidence

ORD record
ord-8574b49b2f8447a4ba0de41419209308
Source dataset
uspto-grants-2011_11
Patent number
US08058444B2

Reaction notes

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