Malonic Acid → HCID 53987483, compound

HRID 613598Notes

Reaction equation

HRID 613598 reaction equation
[C:1]([NH:4][C:5]1[CH:12]=[CH:11][C:8]([CH:9]=O)=[CH:7][C:6]=1[CH3:13])(=[O:3])[CH3:2].C(O)(=O)[CH2:15][C:16]([OH:18])=[O:17].N1C=CC=CC=1>C(O)C>[C:1]([NH:4][C:5]1[CH:12]=[CH:11][C:8]([CH:9]=[CH:15][C:16]([OH:18])=[O:17])=[CH:7][C:6]=1[CH3:13])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 867Malonic AcidHCID 1049PyridineHCID 18321914N-(4-Formyl-2-methylphenyl)acetamide

Product 1

HCID 53987483HCID 53987483, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A mixture of 4-acetamido-3-methylbenzaldehyde (1.23 g), malonic acid (795 mg), pyridine (549 mg) and ethanol (1.7 ml) was refluxed for 3 hours under nitrogen atmosphere. To the mixture was added ethanol (1.7 ml), and the mixture was stirred for 30 minutes under ice-bath cooling. The resulting precipitate was collected by filtration and washed with ethanol to give 4-acetamido-3-methylcinnamic acid (1.08 g).

Workup

  1. temperaturewas refluxed for 3 hours under nitrogen atmosphere
  2. temperaturecooling
  3. filtrationThe resulting precipitate was collected by filtration
  4. washwashed with ethanol

Sources & evidence

ORD record
ord-1f78980c3d6c45429d21d91b15e26853
Source dataset
uspto-grants-1999_12
Patent number
US06008229

Reaction notes

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