Sodium Cyanide → 2-Cyanophenylacetic acid

HRID 1196572Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1196572
[N+]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:10][C:11]([OH:13])=[O:12])([O-])=O.[C-:14]#[N:15].[Na+]>[Pd].[OH-].[Na+]>[C:14]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:10][C:11]([OH:13])=[O:12])#[N:15]

Komponenten

5

Edukt 2

HCID 8929Sodium CyanideHCID 77337(2-Nitrophenyl)acetic acid

Produkt 1

HCID 877552-Cyanophenylacetic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 14798Sodium HydroxideLösungsmittel

Versuchsvorschrift

2-Nitrophenylacetic acid (ex Aldrich) (18.1 g) dissolved in 0.1M.aq.sodium hydroxide (100 ml) was subjected to catalytic hydrogenation (at 30-40 psi) over 10% palladium on charcoal (2 g) until uptake ceased. The resultant solution was subjected first to diazotisation and then reaction with sodium cyanide and cuprous cyanide according to Simchen and Hafner, Ann. Chem., 1974, 1802 to give crude 2-cyanophenylacetic acid (14.9 g). The latter was treated with phosphorous pentachloride (20.6 g) and anhydrous hydrogen chloride in di-n-butyl ether (250 ml) for 2 hours. After a further 18 hours the volatiles were removed, the residue washed with water and recrystallized from ethanol to give 1-chloro-3-hydroxy-isoquinoline (1.48 g).

Quellen und Nachweise

ORD-Eintrag
ord-9c46674a505443329b8f608854c3f72f
Quelldatensatz
uspto-grants-1992_05
Patentnummer
US05114940

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