Malonic Acid → 3-{3-Nitro-4-methoxyphenyl}acrylic acid

HRID 470610

Reaction equation

HRID 470610 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH:7]=O)=[CH:5][C:4]=1[N+:11]([O-:13])=[O:12].C(O)(=O)[CH2:15][C:16]([OH:18])=[O:17].N1CCCCC1>N1C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH:7]=[CH:15][C:16]([OH:18])=[O:17])=[CH:5][C:4]=1[N+:11]([O-:13])=[O:12]

Participants

5

Reactant 3

HCID 867Malonic AcidHCID 8082PiperidineHCID 7006084-Methoxy-3-nitrobenzaldehyde

Product 1

HCID 8217463-{3-Nitro-4-methoxyphenyl}acrylic acid

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent3×

Conditions

Temperature
120 °C

Procedure

4-methoxy-3-nitro-benzaldehyde (compound of Example 5; 1.05 g, 5.79 mmol) and malonic acid (1.32 g, 1.27 mmol) were dissolved in pyridine (20 mL) under stirring and piperidine (1 mL) was added to the pyridine solution. The reaction mixture was heated at 75° C. to 80° C. for 3 h, after which the temperature was further increased to 120° C. and maintained at this temperature for 6 h. At the end of the reaction, pyridine was evaporated, followed by addition of aqueous HCl (1:1) to obtain pH ˜4. The solid obtained was filtered, washed with cold water and dried.

Workup

  1. temperatureThe reaction mixture was heated at 75° C. to 80° C. for 3 h
  2. temperaturemaintained at this temperature for 6 h
  3. customwas evaporated
  4. additionfollowed by addition of aqueous HCl (1:1)
  5. customto obtain pH ˜4
  6. customThe solid obtained
  7. filtrationwas filtered
  8. washwashed with cold water
  9. customdried

Sources & evidence

ORD record
ord-c9716e3dc2f346b3bd78114fc4c8aab5
Source dataset
uspto-grants-2014_01
Patent number
US08629277B2

Linked notes

Loading…