Water → 1-(1-Amino-1H-pyrrol-2-yl)ethanone
Reaction equation
[C:1]([C:4]1[N:5]([N:9]2C(=O)C3C(=CC=CC=3)C2=O)[CH:6]=[CH:7][CH:8]=1)(=[O:3])[CH3:2].CN.O>CN(C)C=O>[NH2:9][N:5]1[CH:6]=[CH:7][CH:8]=[C:4]1[C:1](=[O:3])[CH3:2]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a suspension of 2-(2-acetyl-1H-pyrrol-1-yl)-1H-isoindole-1,3(2H)dione (8.53 g) in dimethylformamide (25 ml) was added 33 ml of 40% methylamine solution. After 2.5 hours, the reaction mixture was poured into water (300 ml) and was extracted 4 times with EtOAc. The combined organics were washed once with water and brine, dried (MgSO4), filtered and concentrated to give the crude product. Purification via flash column chromatography (silica gel, 30% EtOAc/hexane) afforded 3.88 g of the product as an oil.
Workup
- extractionwas extracted 4 times with EtOAc
- washThe combined organics were washed once with water and brine
- dry with materialdried (MgSO4)
- filtrationfiltered
- concentrationconcentrated
- customto give the crude product
- customPurification via flash column chromatography (silica gel, 30% EtOAc/hexane)
Sources & evidence
- ORD record
- ord-b14709ea61d846a78180e562f3dadce8
- Source dataset
- uspto-grants-1997_02
- Patent number
- US05605925
Reaction notes
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