4-(2-Bromoethoxy)benzonitrile → N-[2-(4-cyanophenoxy)ethyl]phthalimide

HRID 323982Notes

Reaction equation

HRID 323982 reaction equation
Br[CH2:2][CH2:3][O:4][C:5]1[CH:12]=[CH:11][C:8]([C:9]#[N:10])=[CH:7][CH:6]=1.[C:13]1(=[O:23])[NH:17][C:16](=[O:18])[C:15]2=[CH:19][CH:20]=[CH:21][CH:22]=[C:14]12.[K]>CN(C=O)C>[C:9]([C:8]1[CH:11]=[CH:12][C:5]([O:4][CH2:3][CH2:2][N:17]2[C:16](=[O:18])[C:15]3=[CH:19][CH:20]=[CH:21][CH:22]=[C:14]3[C:13]2=[O:23])=[CH:6][CH:7]=1)#[N:10]

Participants

4

Reactant 2

HCID 24522124-(2-Bromoethoxy)benzonitrileHCID 24194345Phthalimide potassium salt

Product 1

HCID 8150643N-[2-(4-cyanophenoxy)ethyl]phthalimide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
95 °C

Procedure

4-(2-Bromoethoxy)benzonitrile (7.3 g) was reacted with potassium phthalimide (5.98 g) in DMF (35 ml) by heating at 95° C. for 3 hours. The N-[2-(4-cyanophenoxy) ethyl]phthalimide obtained after extractive workup (7.30 g) was suspended in IMS (350 ml) and treated with hydrazine hydrate (6.25 g). The mixture was stirred for 22 hours and filtered. The solid obtained was washed with IMS and the combined filtrate and washings were evaporated to dryness. Water was added to this residue and the mixture basified with 10M sodium hydroxide solution. The mixture was extracted with dichloromethane to give 4-(2-aminoethoxy)benzonitrile as an oil.

Sources & evidence

ORD record
ord-0e7042f321da4170ac9caa9114453ff0
Source dataset
uspto-grants-2001_04
Patent number
US06215001B1

Reaction notes

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