Hydrochloric Acid → methyl 3-[2-((E)-2-carboxyethenyl)pyrrol-1-yl)benzoate

HRID 399857Notes

Reaction equation

HRID 399857 reaction equation
[CH:1]([C:3]1[N:4]([C:8]2[CH:9]=[C:10]([CH:15]=[CH:16][CH:17]=2)[C:11]([O:13][CH3:14])=[O:12])[CH:5]=[CH:6][CH:7]=1)=O.C(O)(=O)[CH2:19][C:20]([OH:22])=[O:21].N1CCCCC1.Cl>O.N1C=CC=CC=1>[C:20](/[CH:19]=[CH:1]/[C:3]1[N:4]([C:8]2[CH:9]=[C:10]([CH:15]=[CH:16][CH:17]=2)[C:11]([O:13][CH3:14])=[O:12])[CH:5]=[CH:6][CH:7]=1)([OH:22])=[O:21]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 867Malonic AcidHCID 8082PiperidineHCID 17604923methyl 3-(2-formyl-1H-pyrrol-1-yl)benzoate

Product 1

HCID 18945328methyl 3-[2-((E)-2-carboxyethenyl)pyrrol-1-yl)benzoate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent

Procedure

The mixture of methyl 3-(2-formylpyrrol-1-yl)benzoate (3.0 g), malonic acid (2.7 g), pyridine (30 ml) and piperidine (0.3 ml) was stirred for 3 hours at 90°-100° C. The reaction mixture was poured into water, and the mixture was adjusted to pH 1 with 6N-hydrochloric acid. The mixture was extracted with a mixture of ethyl acetate and tetrahydrofuran. The extract layer was washed with brine, dried over magnesium sulfate and evaporated in vacuo. The residue was recrystallized from ethanol to give methyl 3-[2-((E)-2-carboxyethenyl)pyrrol-1-yl)benzoate.

Workup

  1. extractionThe mixture was extracted with a mixture of ethyl acetate and tetrahydrofuran
  2. washThe extract layer was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated in vacuo
  5. customThe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-b5e5e00ad4b44ed78c44a763bfde3e3e
Source dataset
uspto-grants-1998_10
Patent number
US05824691

Reaction notes

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