Dimethylformamide → Methyl 3-(2-carbamoylpyrrol-1-yl)benzoate

HRID 399819Notes

Reaction equation

HRID 399819 reaction equation
[NH4+].[OH-].ClC(Cl)(Cl)[C:5]([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)=[O:6].C[N:25](C)C=O.C(OCC)(=O)C>O>[C:5]([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)(=[O:6])[NH2:25]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8857Ethyl AcetateHCID 14923Ammonium HydroxideHCID 18945198Methyl 3-(2-trichloroacetylpyrrol-1-yl)benzoate

Product 1

HCID 18945445Methyl 3-(2-carbamoylpyrrol-1-yl)benzoate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

28% Ammonia aqueous solution (0.4 ml) was added to a mixture of methyl 3-(2-trichloroacetylpyrrol-1-yl)benzoate (1.0 g) and N,N-dimethylformamide (2 ml), and the mixture was stirred for 1.5 hours at ambient temperature. The mixture was poured into a mixture of ethyl acetate and water. The separated organic layer was washed with water, dried over magnesium sulfate and evaporated in vacuo. The residue was triturated with diisopropyl ether to give methyl 3-(2-carbamoylpyrrol-1-yl)benzoate (0.61 g).

Workup

  1. washThe separated organic layer was washed with water
  2. dry with materialdried over magnesium sulfate
  3. customevaporated in vacuo
  4. customThe residue was triturated with diisopropyl ether

Sources & evidence

ORD record
ord-c7cb23aa2e8f47fd8db795ff3d1f02f4
Source dataset
uspto-grants-1998_10
Patent number
US05824691

Reaction notes

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