Hydrochloric Acid → HCID 17948435, Verbindung

HRID 49221Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 49221
[CH3:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:13](=O)[NH:12][CH:11]=2)=[CH:4][CH:3]=1.P(Cl)(Cl)([Cl:23])=O.Cl.O.N>C(#N)C.O1CCOCC1.CCOC(C)=O>[Cl:23][C:13]1[C:14]2[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:10]([CH2:9][CH2:8][C:5]2[CH:6]=[N:7][C:2]([CH3:1])=[CH:3][CH:4]=2)=[CH:11][N:12]=1

Komponenten

8

Edukt 4

HCID 313Hydrochloric AcidHCID 24813Phosphorus oxychlorideHCID 12896473Azane;hydrateHCID 20636413HCID 20636413, Verbindung

Produkt 1

HCID 17948435HCID 17948435, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6342AcetonitrileLösungsmittelHCID 8857Ethyl AcetateLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

3.12 g (11.8 mmol) of 4-[2-(6-methyl-pyridin-3-yl)-ethyl]-2H-isoquinolin-1-one in 48 ml of acetonitrile are mixed, whilst excluding air, with 3.7 ml (40 mmol) of phosphorus oxychloride and 6 ml of 4 N HCl in dioxane and stirred for 18 h at 55° C. After cooling to RT, water/NH3 conc. 10:1 (pH=9) and EtOAc are added, the water phase is separated and extraction effected twice with EtOAc. The organic phases are washed with water and brine, dried (Na2SO4) and concentrated by evaporation to form 1-chloro-4-[2-(6-methyl-pyridin-3-yl)-ethyl]-isoquinoline; 1H NMR (DMSO-d6) δ8.3 (m, 3H), 8.09 (s, 1H), 7.94 (t, 1H), 7.83 (t, 1H), 7.56 (d, 1H), 7.15 (d, 1H), 3.30 (t, H2C), 2.94 (t, H2C), 2.40 (s, H3C).

Aufarbeitung

  1. customthe water phase is separated
  2. extractionextraction
  3. washThe organic phases are washed with water and brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated by evaporation

Quellen und Nachweise

ORD-Eintrag
ord-9e700d7bf8a146db9092846804668857
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06706731B2

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