N-bromobutanimide → 8-bromo-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline 1-ethyl carboxylate

HRID 1969992Notes

Reaction equation

HRID 1969992 reaction equation
[Br:1]N1C(=O)CCC1=O.[O:9]=[C:10]1[C:19]2[NH:20][CH:21]=[CH:22][C:18]=2[C:17]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[NH:11]1.[CH2:23]([C:25]([O-:27])=[O:26])[CH3:24]>CN(C)C=O.C(OCC)(=O)C>[Br:1][C:15]1[CH:14]=[CH:13][C:12]2[NH:11][C:10](=[O:9])[C:19]3[NH:20][CH:21]=[CH:22][C:18]=3[C:17]=2[CH:16]=1.[CH2:23]([C:25]([O-:27])=[O:26])[CH3:24]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 86627461HCID 86627461, compound

Product 1

HCID 866275178-bromo-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline 1-ethyl carboxylateYield 55%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

434 mg (2.44 mmol) of N-bromosuccinimide is added to 500 mg (1.95 mmol) of 4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-ethyl carboxylate (synthesis 1) dissolved in 10 ml of anhydrous dimethylformamide and the reaction mixture is stirred for 1 h at room temperature. The mixture is then diluted in 10 mL of ethyl acetate, the solid is filtered, rinsed with diethyl ether then recrystallized from acetic acid to give 360 mg (55%) of 8-bromo-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-ethyl carboxylate cocrystallized with one equivalent of acetic acid in the form of a white solid.

Workup

  1. filtrationthe solid is filtered
  2. washrinsed with diethyl ether
  3. customthen recrystallized from acetic acid

Sources & evidence

ORD record
ord-25c3530d616540fcab0408086ad28995
Source dataset
uspto-grants-2013_04
Patent number
US08426437B2

Reaction notes

Loading…