Water → 1-(1-Amino-1H-pyrrol-2-yl)ethanone

HRID 1451977

Reaction equation

HRID 1451977 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

HCID 962WaterHCID 6329MethylamineHCID 199667522-(2-Acetyl-1H-pyrrol-1-yl)-1H-isoindole-1,3(2H)dione

Product 1

HCID 199667441-(1-Amino-1H-pyrrol-2-yl)ethanoneYield 93.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

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

  1. extractionwas extracted 4 times with EtOAc
  2. washThe combined organics were washed once with water and brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give the crude product
  7. 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

Linked notes

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