Formaldehyde → Methyl 3-(2-dimethylaminomethylpyrrol-1-yl)benzoate

HRID 399816Notes

Reaction equation

HRID 399816 reaction equation
[N:1]1([C:6]2[CH:7]=[C:8]([CH:13]=[CH:14][CH:15]=2)[C:9]([O:11][CH3:12])=[O:10])[CH:5]=[CH:4][CH:3]=[CH:2]1.Cl.[CH3:17][NH:18][CH3:19].[CH2:20]=O>C(O)C>[CH3:17][N:18]([CH2:20][C:5]1[N:1]([C:6]2[CH:7]=[C:8]([CH:13]=[CH:14][CH:15]=2)[C:9]([O:11][CH3:12])=[O:10])[CH:2]=[CH:3][CH:4]=1)[CH3:19]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 10473Dimethylamine, hydrochlorideHCID 3322314Methyl 3-(1H-pyrrol-1-yl)benzoate

Product 1

HCID 18945174Methyl 3-(2-dimethylaminomethylpyrrol-1-yl)benzoateYield 59.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The mixture of methyl 3-(pyrrol-1-yl)benzoate (20.0 g), dimethylamine hydrochloride (12.2 g) and paraformaldehyde (13.4 g) in ethanol (60 ml) was heated under reflux for 3 hours under stirring. The solvent was removed by concentration and the residue was added to the mixture of ethyl acetate and water. The mixture was adjusted to pH 12 with 5N-sodium hydroxide solution. The separated organic layer was washed with brine, dried over magnesium sulfate, and evaporated. The residue was purified by column chromatography on silica gel eluting with a mixture of chloroform and methanol (9:1, V/V). The eluted fractions containing the desired product were collected and evaporated in vacuo to give methyl 3-(2-dimethylaminomethylpyrrol-1-yl)benzoate (15.3 g) as an oil.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 3 hours
  3. customThe solvent was removed by concentration
  4. additionthe residue was added to the mixture of ethyl acetate and water
  5. washThe separated organic layer was washed with brine
  6. dry with materialdried over magnesium sulfate
  7. customevaporated
  8. customThe residue was purified by column chromatography on silica gel eluting with a mixture of chloroform and methanol (9:1, V/V)
  9. additionThe eluted fractions containing the desired product
  10. customwere collected
  11. customevaporated in vacuo

Sources & evidence

ORD record
ord-16ccb861e0dc46768c90517d7ff7ce1c
Source dataset
uspto-grants-1998_10
Patent number
US05824691

Reaction notes

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