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Dichloromethane → 2-Benzoyl-5-bromo-1-cyano-1,2-dihydroisoquinoline

HRID 2192468
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2192468
[Br:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][N:6]=[CH:7]2.ClCCl.C[Si]([C:19]#[N:20])(C)C.[C:21](Cl)(=[O:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>[Cl-].[Al+3].[Cl-].[Cl-].O>[Br:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][N:6]([C:21]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:28])[CH:7]2[C:19]#[N:20]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 6344DichloromethaneHCID 7412Benzoyl chlorideHCID 82115Trimethylsilyl cyanideHCID 7364875-Bromoisoquinoline

Produkt 1

HCID 112677672-Benzoyl-5-bromo-1-cyano-1,2-dihydroisoquinolineAusbeute 59,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6451240
Aluminum(III) Chloride
Katalysator
HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
30 °C

Versuchsvorschrift

A round bottomed flask was charged with 5-bromoisoquinoline (available from Aldrich; 4 g, 19.2 mmol), dichloromethane (DCM) (50 ml), trimethylsilyl cyanide (4.81 ml, 38.5 mmol) and aluminium chloride (15 mg, 0.112 mmol). To the mixture was added benzoyl chloride (4.46 ml, 38.5 mmol) slowly over a period of 5 minutes. The mixture was warmed to 30° C. for 3 h after which time it was treated with water (50 ml) and stirred at room temperature for 30 minutes. The organic layers were collected and washed sequentially with 2N HCl, 2N NaOH and brine. The organic layers were passed through a hydrophobic frit before being concentrated in vacuo to give an orange solid. The solid was triturated with diethyl ether and the slurry filtered. The isolated solid was dried in vacuo to give the title compound as a grey solid (3.9 g).

Aufarbeitung

  1. customThe organic layers were collected
  2. washwashed sequentially with 2N HCl, 2N NaOH and brine
  3. concentrationbefore being concentrated in vacuo
  4. customto give an orange solid
  5. customThe solid was triturated with diethyl ether
  6. filtrationthe slurry filtered
  7. customThe isolated solid was dried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-3f48117fbc224cc8a1811c99ceec2977
Quelldatensatz
uspto-grants-2012_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08329730B2

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