Acetic Acid → Ethyl 3-(2,5-dimethyl-1H-pyrrol-1-yl)benzoate

HRID 399795Notes

Reaction equation

HRID 399795 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][CH:12]=1)[C:5]([O:7][CH2:8][CH3:9])=[O:6].[CH3:13][C:14](=O)[CH2:15][CH2:16][C:17](=O)[CH3:18].C(O)(=O)C.O>C1C=CC=CC=1>[CH3:18][C:17]1[N:1]([C:2]2[CH:3]=[C:4]([CH:10]=[CH:11][CH:12]=2)[C:5]([O:7][CH2:8][CH3:9])=[O:6])[C:14]([CH3:13])=[CH:15][CH:16]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 80352,5-HexanedioneHCID 11400Ethyl 3-aminobenzoate

Product 1

HCID 905752Ethyl 3-(2,5-dimethyl-1H-pyrrol-1-yl)benzoate

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

The mixture of ethyl 3-aminobenzoate (2.0 g), hexane-2,5-dione (1.8 ml) and acetic acid (0.7 ml) in benzene (10.0 ml) was heated under reflux for 5 hours, while water was removed in a Dean-Stark apparatus. To the mixture was added a mixture of ethyl acetate and water and the mixture was adjusted to pH 8 with potassium carbonate. The separated organic layer was washed with a brine, dried over magnesium sulfate and evaporated in vacuo to give ethyl 3-(2,5-dimethylpyrrol-1-yl)benzoate (2.9 g) as an oil.

Workup

  1. temperaturewas heated
  2. customwas removed in a Dean-Stark apparatus
  3. additionTo the mixture was added
  4. additiona mixture of ethyl acetate and water
  5. washThe separated organic layer was washed with a brine
  6. dry with materialdried over magnesium sulfate
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-0394619b904d48a7a7935a8b153f07ee
Source dataset
uspto-grants-1998_10
Patent number
US05824691

Reaction notes

Loading…