Sulfuric Acid → 5-Bromo-1,3-dichloroisoquinoline

HRID 2090057

Reaktionsgleichung

Reaktionsgleichung von HRID 2090057
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[C:4]([Cl:12])[N:3]=1.S(=O)(=O)(O)O.[Br:18]N1C(=O)CCC1=O>CC#N>[Br:18][C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:6]=1[CH:5]=[C:4]([Cl:12])[N:3]=[C:2]2[Cl:1]

Komponenten

5

Edukt 3

HCID 1118Sulfuric AcidHCID 67184N-bromobutanimideHCID 2986251,3-Dichloroisoquinoline

Produkt 1

HCID 205790315-Bromo-1,3-dichloroisoquinoline

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

To a solution of 1,3-dichloroisoquinoline (1.0 g, 5.1 mmol) in CH3CN (25 mL) was added concentrated sulfuric acid (1.0 mL, 18 mmol), followed by N-bromosuccinimide (1.1 g, 6.1 mmol). The mixture was stirred at room temperature for 60 hours. The precipitate was collected by filtration, washed with water, then dried in air to afford the title compound: 1H NMR (500 MHz, CDCl3): δ 8.35 (d, J=9.0 Hz, 1H), 8.09 (s, 1H), 8.08 (d, J=9.0 Hz, 1H), 7.57 (t, J=8.0 Hz, 1H). LC6: 3.74 min. (M+H): 278.

Aufarbeitung

  1. filtrationThe precipitate was collected by filtration
  2. washwashed with water
  3. customdried in air

Quellen und Nachweise

ORD-Eintrag
ord-562b6eda41a041f6b3d0e9dc14d4aff1
Quelldatensatz
uspto-grants-2013_05
Patentnummer
US08436015B2

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