2,4-Dimethylbenzylamine → 6,8-Dimethylisoquinolin-3-amine

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Reaktionsgleichung

C(O[CH:4](OCC)[C:5](=[NH:8])OC)C.[CH3:12][C:13]1[CH:18]=[C:17]([CH3:19])[CH:16]=[CH:15][C:14]=1[CH2:20][NH2:21]>CO>[CH3:19][C:17]1[CH:16]=[C:15]2[C:4](=[C:13]([CH3:12])[CH:18]=1)[CH:5]=[N:8][C:20]([NH2:21])=[CH:14]2

Komponenten

Reaktionsbedingungen

Temperatur: 70 °C

Versuchsvorschrift

To a solution of methyl 2,2-diethoxyacetimidate (1.5 g, 9.3 mmol) in methanol (4.9 mL) was added (2,4-dimethylphenyl)methanamine (1.2 g, 8.9 mmol) dropwise at ambient temperature. The reaction flask was then placed into a preheated oil-bath and stirred at 70° C. for 16 h, then cooled and the volatiles removed under reduced pressure. The crude material was added dropwise to sulfuric acid (19.7 mL) at ambient temperature and stirred for 72 h. The flask was then placed into an ice-water bath, diluted with water (50 mL), and slowly neutralized to pH=10 with sodium hydroxide (10 N). As the reaction mixture became basic, an orange precipitate formed. This precipitate was filtered, washed with water, and dried to afford 6,8-dimethylisoquinolin-3-amine (1.37 g, 7.95 mmol, 90%). 1H NMR (400 MHz, MeOD) δ ppm 8.82 (s, 1H), 7.17 (s, 1H), 6.90 (s, 1H), 6.72 (s, 1H), 2.61 (s, 3H), 2.37 (s, 3H). MS (LC/MS) R.T.=0.77; [M+H]+=173.15.

Aufarbeitung

customThe reaction flask was then placed into a preheated oil-bath
temperaturecooled
customthe volatiles removed under reduced pressure
additionThe crude material was added dropwise to sulfuric acid (19.7 mL) at ambient temperature
stirringstirred for 72 h
customThe flask was then placed into an ice-water bath
additiondiluted with water (50 mL)
customan orange precipitate formed
filtrationThis precipitate was filtered
washwashed with water
customdried

Quellen und Nachweise

ORD-Eintrag: ord-ef5c9351941e43ea823dd64cd92184db
Quelldatensatz: uspto-grants-2011_01
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07863291B2

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