Benzonitrile, m-chloro- → 7-bromo-3-(3-chlorophenyl)isoquinolin-1(2H)-one

HRID 77388

Reaktionsgleichung

C([N-]C(C)C)(C)C.[Li+].[Br:9][C:10]1[CH:11]=[CH:12][C:13]([CH3:20])=[C:14]([CH:19]=1)[C:15]([NH:17][CH3:18])=[O:16].[Cl:21][C:22]1[CH:23]=[C:24]([CH:27]=[CH:28][CH:29]=1)C#N.[NH4+].[Cl-]>O1CCCC1>[Br:9][C:10]1[CH:19]=[C:14]2[C:13]([CH:20]=[C:18]([C:28]3[CH:27]=[CH:24][CH:23]=[C:22]([Cl:21])[CH:29]=3)[NH:17][C:15]2=[O:16])=[CH:12][CH:11]=1

Komponenten

Reaktionsbedingungen

Temperatur: -78 °C

Versuchsvorschrift

To a solution of 2M lithium diisopropylamide (19.73 mL, 39.5 mmol) in tetrahydrofuran (30 mL) at −78° C. was added dropwise a solution of 5-bromo-N,2-dimethylbenzamide (Intermediate 22A) (3.0 g, 13.15 mmol) in THF (14 mL) followed by a solution of 3-chlorobenzonitrile (1.809 g, 13.15 mmol) in THF (14 mL) and the mixture was stirred at −78° C. for 2.5 hours. Reaction allowed to warm to room temperature and saturated NH4Cl (aq) was added. The THF was removed under reduced pressure and the resulting mixture extracted into ethyl acetate and washed with brine (precipitate was observed in both layers). Organics were evaporated to dryness, washed with methanol and dried in a vacuum oven to afford 7-bromo-3-(3-chlorophenyl)isoquinolin-1(2H)-one (0.9 g, 2.69 mmol).

Aufarbeitung

customReaction
temperatureto warm to room temperature
customThe THF was removed under reduced pressure
extractionthe resulting mixture extracted into ethyl acetate
washwashed with brine (precipitate
customOrganics were evaporated to dryness
washwashed with methanol
customdried in a vacuum oven

Quellen und Nachweise

ORD-Eintrag: ord-d4f48ef7718646d88df61971e710820c
Quelldatensatz: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08841289B2

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