Isobutylamine → 2-(2-Methylpropyl)-1H-isoindole-1,3(2H)-dione

HRID 733210Notes

Reaction equation

HRID 733210 reaction equation
[CH2:1]([NH2:5])[CH:2]([CH3:4])[CH3:3].[C:6]1(=O)[O:11][C:9](=[O:10])[C:8]2=[CH:12][CH:13]=[CH:14][CH:15]=[C:7]12>C1(C)C=CC=CC=1>[CH2:1]([N:5]1[C:9](=[O:10])[C:8]2=[CH:12][CH:13]=[CH:14][CH:15]=[C:7]2[C:6]1=[O:11])[CH:2]([CH3:4])[CH3:3]

Participants

4

Reactant 2

HCID 6558IsobutylamineHCID 6811Phthalic Anhydride

Product 1

HCID 963802-(2-Methylpropyl)-1H-isoindole-1,3(2H)-dione

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
60 °C

Procedure

A solution of 3.2 cm3 of isobutylamine in 3 cm3 of toluene is added to a suspension of 5.2 g of phthalic anhydride in 50 cm3 of toluene, with stirring. The reaction mixture is heated at a temperature in the region of 60° C. for 1 hour, and then at a temperature in the region of 100° C. for 2 hours. Dean-Stark apparatus is then installed on the reactor and the reaction mixture is heated at a temperature in the region of 130° C. for 2 hours, after which it is cooled to a temperature in the region of 20° C. The reaction mixture is concentrated to dryness under reduced pressure (2 kPa) at a temperature in the region of 40° C. The residue is taken up in 50 cm3 of saturated sodium bicarbonate solution and extracted twice with 75 cm3 of dichloromethane. The organic extracts are combined, dried over magnesium sulfate, filtered and then concentrated to dryness under reduced pressure (2 kPa) at a temperature in the region of 20° C. 6.5 g of N-isobutylphthalimide are thus obtained in the form of a white solid melting at 92° C.

Workup

  1. temperaturethe reaction mixture is heated at a temperature in the region of 130° C. for 2 hours
  2. temperatureafter which it is cooled to a temperature in the region of 20° C
  3. concentrationThe reaction mixture is concentrated to dryness under reduced pressure (2 kPa) at a temperature in the region of 40° C
  4. extractionextracted twice with 75 cm3 of dichloromethane
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated to dryness under reduced pressure (2 kPa) at a temperature in the region of 20° C

Sources & evidence

ORD record
ord-da099354130c4a4d8a31609d72a74297
Source dataset
uspto-grants-2009_09
Patent number
US07589117B2

Reaction notes

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