Nitromethane → HCID 59255093, compound

HRID 1891689Notes

Reaction equation

HRID 1891689 reaction equation
[CH:1]1([CH2:4][O:5][C:6]2[CH:7]=[C:8]([CH:11]=[CH:12][CH:13]=2)[CH:9]=O)[CH2:3][CH2:2]1.[N+:14]([CH3:17])([O-:16])=[O:15].C([O-])(=O)C.[NH4+]>C(O)(=O)C>[CH:1]1([CH2:4][O:5][C:6]2[CH:13]=[CH:12][CH:11]=[C:8](/[CH:9]=[CH:17]/[N+:14]([O-:16])=[O:15])[CH:7]=2)[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 6375NitromethaneHCID 517165Ammonium AcetateHCID 220482703-(Cyclopropylmethoxy)benzaldehyde

Product 1

HCID 59255093HCID 59255093, compoundYield 69.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 3-cyclopropylmethoxy-benzaldehyde (4.32 g, 24.5 mmol) described in Manufacturing Example 66-1-1, nitromethane (2.64 mL, 49 mmol), ammonium acetate (2.83 g, 36.8 mmol) and acetic acid (40 mL) was stirred for 5 hours at 100° C. This mixture was cooled to room temperature, concentrated under a reduced pressure, and diluted 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, and the residue was purified by silica gel column chromatography (heptane:ethyl acetate=4:1-1:1) to obtain the title compound (3.73 g, 69%).

Workup

  1. temperatureThis mixture was cooled to room temperature
  2. concentrationconcentrated under a reduced pressure
  3. additiondiluted with ethyl acetate
  4. washThe organic layer was washed with water and saturated aqueous sodium chloride
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated under a reduced pressure
  8. customthe residue was purified by silica gel column chromatography (heptane:ethyl acetate=4:1-1:1)

Sources & evidence

ORD record
ord-de9c9f0b5c61434faed2bfd64fe82b7a
Source dataset
uspto-grants-2013_08
Patent number
US08507530B2

Reaction notes

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