Sulfuric Acid → 8-Bromo-5-fluoroisoquinolin-3-amine

HRID 1876037Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1876037
[Br:1][C:2]1[CH:18]=[CH:17][C:16]([F:19])=[CH:15][C:3]=1[CH2:4][NH:5][C:6](=[NH:14])[CH:7](OCC)OCC.ClCCl.OS(O)(=O)=O>CCOC(C)=O>[Br:1][C:2]1[CH:18]=[CH:17][C:16]([F:19])=[C:15]2[C:3]=1[CH:4]=[N:5][C:6]([NH2:14])=[CH:7]2

Komponenten

5

Edukt 3

HCID 1118Sulfuric AcidHCID 6344DichloromethaneHCID 178471679HCID 178471679, Verbindung

Produkt 1

HCID 534189908-Bromo-5-fluoroisoquinolin-3-amine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a mixture of N-(2-bromo-5-fluorobenzyl)-2,2-diethoxyacetimidamide (1.6 g, 4.80 mmol) and dichloromethane (2 mL) was added H2SO4 (1.280 mL, 24.01 mmol). The reaction mixture was stirred at 80° C. for 16 hours, cooled to rt., diluted with EtOAc (100 mL), quenched with ice-water, and neutralized with NaHCO3 solution. The organic phase was washed with water, dried over Na2SO4, and evaporated. The residue was purified on an 80 g Thompson silica cartridge (3% to 100% EtOAc in Hexanes, 1200 mL). The desired product was obtained as a pale yellow solid (0.47 g, 1.950 mmol, 40.6% yield).

Aufarbeitung

  1. temperaturecooled to rt
  2. customquenched with ice-water
  3. washThe organic phase was washed with water
  4. dry with materialdried over Na2SO4
  5. customevaporated
  6. customThe residue was purified on an 80 g Thompson silica cartridge (3% to 100% EtOAc in Hexanes, 1200 mL)

Quellen und Nachweise

ORD-Eintrag
ord-a3dcea4a1b77486684b50fc5e5ec3928
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08309577B2

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