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

HRID 2268269Notes

Reaction equation

HRID 2268269 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-5e3adb67b43a4056947d29d8e1fcd10d
Source dataset
uspto-grants-2001_12
Patent number
US06326500B1

Reaction notes

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