Water → [3-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-5-methyl-phenoxy]-acetonitrile

HRID 482253Notes

Reaction equation

HRID 482253 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([N:9]2[C:17](=[O:18])[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10]2=[O:19])[CH:5]=[C:6]([CH3:8])[CH:7]=1.Cl[CH2:21][C:22]#[N:23].C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[O:18]=[C:17]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10](=[O:19])[N:9]1[C:4]1[CH:3]=[C:2]([CH:7]=[C:6]([CH3:8])[CH:5]=1)[O:1][CH2:21][C:22]#[N:23]

Participants

6

Reactant 4

HCID 962WaterHCID 7856ChloroacetonitrileHCID 11430Potassium CarbonateHCID 189450002-(3-Hydroxy-5-methyl-phenyl)-isoindole-1,3-dione

Product 1

HCID 18945008[3-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-5-methyl-phenoxy]-acetonitrileYield 89%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

59 g (233 mmol) 2-(3-hydroxy-5-methyl-phenyl)-isoindole-1,3-dione, 44 ml (700 mmol) chloroacetonitrile and 96.7 g (700 mmol) potassium carbonate were heated for 4 h to 80° C. in 300 ml dry dimethyl-formamide. It was poured onto 2 l water, filtered and 60.5 g (89%) [3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-5-methyl-phenoxy]-acetonitrile of Fp 156°-157° C. was obtained.

Workup

  1. filtrationfiltered

Sources & evidence

ORD record
ord-4c7d6a72510544dcab53b149d7d45b30
Source dataset
uspto-grants-1998_08
Patent number
US05795892

Reaction notes

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