Acetic Acid → HCID 59255233, compound

HRID 1891729Notes

Reaction equation

HRID 1891729 reaction equation
C(O)(=O)C.[N:5]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][C:12]2[CH:19]=[CH:18][C:15]([CH:16]=O)=[CH:14][CH:13]=2)[CH:6]=1.[N+:20]([CH3:23])([O-:22])=[O:21].C([O-])(=O)C.[NH4+]>C(OCC)(=O)C.O>[N+:20](/[CH:23]=[CH:16]/[C:15]1[CH:18]=[CH:19][C:12]([O:11][C:7]2[CH:6]=[N:5][CH:10]=[CH:9][CH:8]=2)=[CH:13][CH:14]=1)([O-:22])=[O:21]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 6375NitromethaneHCID 517165Ammonium AcetateHCID 46774194-(Pyridin-3-yloxy)benzaldehyde

Product 1

HCID 59255233HCID 59255233, compoundYield 96.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
110 °C

Procedure

To an acetic acid (17.0 mL) solution of 4-(pyridine-3-yloxy)-benzaldehyde (1.70 g, 8.53 mmol) described in Manufacturing Example 76-1-1 were added nitromethane (2.60 g, 42.7 mmol) and ammonium acetate (1.32 g, 17.1 mmol) under nitrogen atmosphere, which was stirred for 3 hours at 110° C. Water and ethyl acetate were added to the reaction solution, and the organic layer was then extracted with ethyl acetate. The organic layer was washed with water and saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under a reduced pressure to obtain the title compound (2.00 g) as a crude product.

Workup

  1. extractionthe organic layer was then extracted with ethyl acetate
  2. washThe organic layer was washed with water and saturated aqueous sodium chloride
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated under a reduced pressure

Sources & evidence

ORD record
ord-ff0653d896b74bef8e5a6f4f3743d31a
Source dataset
uspto-grants-2013_08
Patent number
US08507530B2

Reaction notes

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