Pentane → HCID 178487736, Verbindung

HRID 1852063Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1852063
C([N:3]([CH2:15][CH3:16])[C:4](=[O:14])[C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][C:6]=1[CH3:13])C.C([Li])(C)(C)C.CCCCC.[CH:27]([O:30][C:31]1[CH:32]=[CH:33]C(C#N)=[N:35][CH:36]=1)([CH3:29])[CH3:28]>C1COCC1>[CH:27]([O:30][C:31]1[CH:32]=[CH:33][C:16]([C:15]2[N:3]=[C:4]([OH:14])[C:5]3[C:6]([CH:13]=2)=[CH:7][C:8]([O:11][CH3:12])=[CH:9][CH:10]=3)=[N:35][CH:36]=1)([CH3:29])[CH3:28]

Komponenten

6

Edukt 4

HCID 8003PentaneHCID 11053218N,N-diethyl-4-methoxy-2-methyl-benzamideHCID 866831725-IsopropoxypicolinonitrileHCID 178418306HCID 178418306, Verbindung

Produkt 1

HCID 178487736HCID 178487736, VerbindungAusbeute 64,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a solution of N,N-diethyl-4-methoxy-2-methylbenzamide (4.43 g, 20 mmol) in THF (100 ml) at −78° C., tert-butyllithium 1.7 M in pentane (17.65 ml, 30.0 mmol) solution was added dropwise. The reaction mixture was stirred for 0.5 h before addition of 5-isopropoxypicolinonitrile (3.41 g, 21.00 mmol) in THF (2 mL). The resulting solution was warmed to rt and stirred for 16 h. The reaction mixture was quenched with water, neutralized with 1 N HCl. The precipitated solid (5 g) was collected and washed with water to give the product 3-(5-isopropoxypyridin-2-yl)-6-methoxyisoquinolin-1-ol 4 g as a white solid. MS: MS m/z 311.11 (M++1).

Aufarbeitung

  1. customThe reaction mixture was quenched with water
  2. customThe precipitated solid (5 g) was collected
  3. washwashed with water

Quellen und Nachweise

ORD-Eintrag
ord-8a6394eed2374d2499f29ef76bb036f6
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08957203B2

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