Sodium Cyanide → Benzofuran-2-carboxylic acid, 5-cyanomethyl-, ethyl ester

HRID 2106793

Reaktionsgleichung

Reaktionsgleichung von HRID 2106793
Cl[CH2:2][C:3]1[CH:16]=[CH:15][C:6]2[O:7][C:8]([C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:9][C:5]=2[CH:4]=1.[C-:17]#[N:18].[Na+]>CN(C)C=O>[C:17]([CH2:2][C:3]1[CH:16]=[CH:15][C:6]2[O:7][C:8]([C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:9][C:5]=2[CH:4]=1)#[N:18]

Komponenten

4

Edukt 2

HCID 8929Sodium CyanideHCID 13322225Ethyl 5-(chloromethyl)-1-benzofuran-2-carboxylate

Produkt 1

HCID 615261Benzofuran-2-carboxylic acid, 5-cyanomethyl-, ethyl esterAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

The starting material can be prepared as follows: By the reaction of ethyl 5-chloromethylbenzo[b]furan-2-carboxylate (Chem. Abstr., 1959, 3185d) with excess sodium cyanide in dimethylformamide there is obtained, in a yield of 90% of theory, ethyl 5-cyanomethylbenzo[b]furan-2-carboxylate (m.p. 74°-76° C. after recrystallisation from ethyl acetate) which is hydrogenated in the presence of platinum oxide to give ethyl 5-(2-aminoethyl)-benzo[b]furan-2-carboxylate. From an ethanolic solution thereof, with an ethereal solution of hydrogen chloride there can be precipitated out the hydrochloride; m.p. 188°-190° C.; yield 64% of theory.

Aufarbeitung

  1. customThe starting material can be prepared

Quellen und Nachweise

ORD-Eintrag
ord-cfe8fea7ba374b2e88bce6f23cc364b5
Quelldatensatz
uspto-grants-1990_06
Patentnummer
US04931462

Verknüpfte Notizen

Wird geladen…