Ethylenediamine → 4-(2-Aminoethyl)benzonitrile

HRID 1249704Notes

Reaction equation

HRID 1249704 reaction equation
F[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1.[CH2:10](N)[CH2:11][NH2:12]>>[NH2:12][CH2:11][CH2:10][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 3301EthylenediamineHCID 145174-Fluorobenzonitrile

Product 1

HCID 219125254-(2-Aminoethyl)benzonitrile

Procedure

4-Fluorobenzonitrile is reacted with an excess of ethylenediamine in an aprotic solvent to give 4-(2-aminoethyl)benzonitrile which is then mono-alkylated with ethyl bromoacetate in a polar solvent such as ethanol or acetonitrile in the presence of an inorganic base or a tertiary amine. Acylation with chloroacetyl chloride followed by cyclization and hydrolysis give the acid (1).

Sources & evidence

ORD record
ord-5b0044c39dfb41589ade3bda6fadf850
Source dataset
uspto-grants-2002_01
Patent number
US06335337B1

Reaction notes

Loading…