Ammonium Chloride → 5-Amino-1-chloroisoquinoline

HRID 908311

Reaktionsgleichung

[CH:1]1[C:10]2[C:5](=[C:6](C3C=C4C(=CC=3)C=C(NC(C3SC=CC=3)=O)C=C4)[CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][N:2]=1.[NH4+:29].[Cl-:30]>[Fe].CCO.O>[Cl:30][C:1]1[C:10]2[CH:9]=[CH:8][CH:7]=[C:6]([NH2:29])[C:5]=2[CH:4]=[CH:3][N:2]=1

Komponenten

Reaktionsbedingungen

Temperatur: 80 °C

Versuchsvorschrift

To a 1000 mL 3-neck round-bottomed flask containing 1-chloro-5-nitroisoquinoline (Step 1, 8.200 g, 39.3 mmol) was added Iron powder (11.80 g, 211.2 mmol), while under a flow of inert gas. A 3:1 mixture of EtOH/H2O (240 mL), and NH4Cl (1.19 g, 22.4 mmol) were added. The mixture was heated to 80° C., while stirring under inert atmosphere for 1 hour. The oil bath was removed and the mixture was allowed to cool to ambient temperature. The crude material was filtered through a plug of Celite, and the filtrate was concentrated in-vacuo. Recrystallization from DCM/Hexanes, and further washing the solid with hexanes (3×100 mL) afforded a brown crystalline solid, which was titled product (7.015 g, 39.3 mmol). MS (ESI pos. ion) m/z: 179 (M+H). Calc'd Exact Mass for C9H7N2Cl: 178.5

Aufarbeitung

additionwere added
customThe oil bath was removed
temperatureto cool to ambient temperature
filtrationThe crude material was filtered through a plug of Celite
concentrationthe filtrate was concentrated in-vacuo
customRecrystallization from DCM/Hexanes
washfurther washing the solid with hexanes (3×100 mL)
customafforded a brown crystalline solid, which

Quellen und Nachweise

ORD-Eintrag: ord-5efaa73899c048bdadd693b8c1e554c6
Quelldatensatz: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08017601B2

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