Phthalic Anhydride → HCID 693739, compound

HRID 522520Notes

Reaction equation

HRID 522520 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[C:5]#[N:6].[C:10]1(=O)[O:15][C:13](=[O:14])[C:12]2=[CH:16][CH:17]=[CH:18][CH:19]=[C:11]12>O1CCOCC1>[O:14]=[C:13]1[C:12]2[C:11](=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:10](=[O:15])[N:1]1[C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[C:5]#[N:6]

Participants

4

Reactant 2

HCID 6811Phthalic AnhydrideHCID 167023-Aminobenzonitrile

Product 1

HCID 693739HCID 693739, compoundYield 50.8%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
0 °C

Procedure

Dissolved 3-aminobenzonitrile (1.5 g, 12.7 mmol) in anhydrous dioxane (42 mL) under N2. Added phthalic anhydride (2.54 g, 17.1 mmol). Affixed Dean-Stark trap and refluxed for 16 h. Cooled to 0° C. and filtered off solid (2-((3-cyanophenyl)carbamoyl)benzoic acid). Concentrated filtrate to afford 3-(1,3-dioxoisoindolin-2-yl)benzonitrile (1.6 g) as a white solid. MS, calc'd=248.06. Obsv'd m/z: 248.91 (M+1).

Workup

  1. temperatureAffixed Dean-Stark trap and refluxed for 16 h
  2. filtrationfiltered off solid (2-((3-cyanophenyl)carbamoyl)benzoic acid)

Sources & evidence

ORD record
ord-27b40731abe24ad7becf033884dc82c0
Source dataset
uspto-grants-2016_05
Patent number
US09334246B2

Reaction notes

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