1,3-Dimethyl-2-imidazolidinone → Methyl 3-(2-methylpyrrol-1-yl)benzoate

HRID 399818Notes

Reaction equation

HRID 399818 reaction equation
[I-].C[N+]([CH2:6][C:7]1[N:8]([C:12]2[CH:13]=[C:14]([CH:19]=[CH:20][CH:21]=2)[C:15]([O:17][CH3:18])=[O:16])[CH:9]=[CH:10][CH:11]=1)(C)C.CN1CCN(C)C1=O>ClCCl>[CH3:6][C:7]1[N:8]([C:12]2[CH:13]=[C:14]([CH:19]=[CH:20][CH:21]=2)[C:15]([O:17][CH3:18])=[O:16])[CH:9]=[CH:10][CH:11]=1

Participants

4

Reactant 2

HCID 66611,3-Dimethyl-2-imidazolidinoneHCID 18945213Methyl 3-(2-trimethylammoniomethylpyrrol-1-yl)benzoate iodide

Product 1

HCID 18945253Methyl 3-(2-methylpyrrol-1-yl)benzoateYield 93.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
105 °C

Procedure

To the mixture of methyl 3-(2-trimethylammoniomethyl-pyrrol-1-yl)benzoate iodide (2.0 g) and 1,3-dimethyl-imidazolidin-2-one (6 ml) was added borane-pyridine complex (1.1 ml) and the mixture was stirred for 1.5 hours at 105° C. To the mixture was added dichloromethane, and the mixture was washed with water, 1N-hydrochloric acid and water successively. The mixture was dried over magnesium sulfate and evaporated in vacuo to give methyl 3-(2-methylpyrrol-1-yl)benzoate (1.01 g) as an oil.

Workup

  1. additionwas added borane-pyridine complex (1.1 ml)
  2. washthe mixture was washed with water, 1N-hydrochloric acid and water successively
  3. dry with materialThe mixture was dried over magnesium sulfate
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-21bd637df8ba45ed83d21a6b8abb44c0
Source dataset
uspto-grants-1998_10
Patent number
US05824691

Reaction notes

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