Water → 2-(2-(Imidazo[1,2-a]pyridin-2-yl)ethyl)isoindoline-1,3-dione

HRID 918336Notes

Reaction equation

HRID 918336 reaction equation
Br[CH2:2][C:3](=O)[CH2:4][CH2:5][N:6]1[C:10](=[O:11])[C:9]2=[CH:12][CH:13]=[CH:14][CH:15]=[C:8]2[C:7]1=[O:16].[NH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=1.C(=O)(O)[O-].[Na+].O>CN(C)C=O.C(O)C>[C:10]1(=[O:11])[N:6]([CH2:5][CH2:4][C:3]2[N:18]=[C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][N:20]3[CH:2]=2)[C:7](=[O:16])[C:8]2=[CH:15][CH:14]=[CH:13][CH:12]=[C:9]12

Participants

7

Reactant 4

HCID 962WaterHCID 104392-AminopyridineHCID 516892Sodium BicarbonateHCID 37597442-(4-Bromo-3-oxobutyl)-1H-isoindole-1,3(2H)-dione

Product 1

HCID 15312692-(2-(Imidazo[1,2-a]pyridin-2-yl)ethyl)isoindoline-1,3-dioneYield 57.7%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6228DimethylformamideSolvent

Procedure

1-Bromo-4-phthalimidobutan-2-one (23.6 g.) was added to a solution of 2-aminopyridine (7.6 g.) and sodium bicarbonate (6.8 g.) in dimethylformamide (100 ml.) and the mixture was heated at 100° for 1 hour. Cooling followed by addition to water and recrystallisation from ethanol afforded 2-(2-phthalimidoethyl)imidazo [1,2-a]-pyridine (13.4 g.) m.p. 181° - 181.5°.

Workup

  1. temperaturethe mixture was heated at 100° for 1 hour
  2. temperatureCooling

Sources & evidence

ORD record
ord-c3942212e0a8463c9bd7333b5bba2a5f
Source dataset
uspto-grants-1976_07
Patent number
US03970753

Reaction notes

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