Toluene → N-(1,3-dioxo-2,3-dihydro-1H-isoindol-2-yl)(tert-butoxy)formamide

HRID 2191897Notes

Reaction equation

HRID 2191897 reaction equation
[NH:1]([C:3]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4])[NH2:2].C1(C)C=CC=CC=1.[C:17]1(=O)[O:22][C:20](=[O:21])[C:19]2=[CH:23][CH:24]=[CH:25][CH:26]=[C:18]12>O>[O:21]=[C:20]1[C:19]2[C:18](=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:17](=[O:22])[N:2]1[NH:1][C:3](=[O:4])[O:5][C:6]([CH3:9])([CH3:8])[CH3:7]

Participants

5

Reactant 3

HCID 1140TolueneHCID 6811Phthalic AnhydrideHCID 70091tert-Butyl carbazate

Product 1

HCID 801162N-(1,3-dioxo-2,3-dihydro-1H-isoindol-2-yl)(tert-butoxy)formamideYield 104.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Tert-butyl hydrazinecarboxylate (250 g) was added to a toluene (3 L) solution of phthalic anhydride (280 g). In a Dean Stark water separator, the reaction mixture was heated under reflux for 3 hours. After cooled to room temperature, the formed solid was collected through filtration to give crude tert-butyl (1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)carbamate (516 g).

Workup

  1. temperatureunder reflux for 3 hours
  2. filtrationthe formed solid was collected through filtration

Sources & evidence

ORD record
ord-3ddc9177cea14a2ca5a16015add60ffe
Source dataset
uspto-grants-2012_12
Patent number
US08329711B2

Reaction notes

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