Hydrochloric Acid → HCID 178511859, Verbindung

HRID 732108

Reaktionsgleichung

Reaktionsgleichung von HRID 732108
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]#[N:9])[CH:5]=[C:4]([Cl:10])[N:3]=1.C[O-].[Na+].Cl.[CH:15]1([NH2:18])[CH2:17][CH2:16]1>CCO.CO>[Cl:1][C:2]1[CH:7]=[C:6]([CH:5]=[C:4]([Cl:10])[N:3]=1)[C:8]([NH:18][CH:15]1[CH2:17][CH2:16]1)=[NH:9]

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 69828CyclopropylamineHCID 7359062,6-DichloroisonicotinonitrileHCID 10942334Sodium Methoxide

Produkt 1

HCID 178511859HCID 178511859, VerbindungAusbeute 57,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 887MethanolLösungsmittel

Versuchsvorschrift

2,6-dichloropyridine-4-carbonitrile (5 g, 28.9 mmol), methanol (50 ml) and sodium methoxide (0.66 ml, 2.89 mmol) were mixed and stirred at r.t. for 3 h. HCl in EtOH (24% w/w, 10 ml) and cyclopropylamine (3 mL, 43.4 mmol) were added at 0° C., followed by stirring at r.t. o.n. The reaction mixture was concentrated in-vacuo. The isolated residue was treated with cold aq. NaOH (1N, 75 ml) and extracted with EA. The combined organic phase was washed sequentially with aq. NaOH and brine, dried (Na2SO4), filtered and concentrated in-vacuo. The isolated residue was triturated with Et2O to isolate the title compound (3.82 g). 1H-NMR: 7.59 (br. s, 2H), 4.96 (br. s, 2H), 2.60 (m, 1H), 0.90 (m, 2H), 0.69 (m, 2H).

Aufarbeitung

  1. stirringby stirring at r.t. o.n
  2. concentrationThe reaction mixture was concentrated in-vacuo
  3. additionThe isolated residue was treated with cold aq. NaOH (1N, 75 ml)
  4. extractionextracted with EA
  5. washThe combined organic phase was washed sequentially with aq. NaOH and brine
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated in-vacuo
  9. customThe isolated residue was triturated with Et2O

Quellen und Nachweise

ORD-Eintrag
ord-e2e554707a4e41a989ac5db57b31e505
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07585881B2

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