HCID 53762775, compound → HCID 19905460, compound

HRID 2371957Notes

Reaction equation

HRID 2371957 reaction equation
[CH3:1][C:2]1[N:3]([C:8]2[CH:19]=[CH:18][C:11]([CH:12]=[CH:13][C:14]([O:16]C)=[O:15])=[CH:10][CH:9]=2)[C:4]([CH3:7])=[CH:5][CH:6]=1>CO.[OH-].[Na+]>[CH3:7][C:4]1[N:3]([C:8]2[CH:19]=[CH:18][C:11](/[CH:12]=[CH:13]/[C:14]([OH:16])=[O:15])=[CH:10][CH:9]=2)[C:2]([CH3:1])=[CH:6][CH:5]=1

Participants

4

Reactant 1

HCID 53762775HCID 53762775, compound

Product 1

HCID 19905460HCID 19905460, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

A mixture of 21.4 g of methyl 4-aminocinnamate and 50 g of acetonylacetone in 500 ml of toluene is heated under reflux using a Dean Stark water separator for 16 hours. The solution is washed with ice cold dilute hydrochloric acid, brine, and then dried over magnesium sulfate. The organic phase is filtered through silica gel, evaporated at 60° under reduced pressure and the residue is crystallized from hexane to yield methyl 4-(2,5-dimethyl-1H-pyrrol-1-yl)-cinnamate, m.p. 73°-75°. A solution of the ester in 150 ml of methanol and 100 ml 1N aqueous sodium hydroxide is stirred at room temperature for 16 hours. Methanol is evaporated at 60° under reduced pressure. The basic solution is washed with ethyl acetate, then made acidic with ice cold 5N aqueous hydroxhloric acid, and extracted with ethyl acetate. The extract is washed with brine, dried over magnesium sulfate, treated with charcoal, and evaporated to dryness at 60° under reduced pressure. The residue is crystallized from ether/hexane (2:1) to yield (E)-4-(2,5-di-methyl-1H-pyrrol-1-yl)-cinnamic acid, m.p. 189°-191°, also named (E)-3-[4-(2,5-dimethyl-1H-pyrrol-1-yl)-phenyl]-2-propenoic acid.

Workup

  1. customMethanol is evaporated at 60° under reduced pressure
  2. washThe basic solution is washed with ethyl acetate
  3. extractionextracted with ethyl acetate
  4. washThe extract is washed with brine
  5. dry with materialdried over magnesium sulfate
  6. additiontreated with charcoal
  7. customevaporated to dryness at 60° under reduced pressure
  8. customThe residue is crystallized from ether/hexane (2:1)

Sources & evidence

ORD record
ord-791030c1e48f499bab1d3778ba6eebfd
Source dataset
uspto-grants-1992_03
Patent number
US05096919

Reaction notes

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