Hydroxyamine hydrochloride → HCID 178463716, Verbindung

HRID 2047283Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2047283
Cl.[NH2:2][OH:3].[CH2:4]([N:6]([CH3:16])[C:7]1[CH:8]=[C:9]([CH:12]=[C:13]([CH3:15])[N:14]=1)[C:10]#[N:11])[CH3:5]>CO>[CH2:4]([N:6]([CH3:16])[C:7]1[CH:8]=[C:9]([CH:12]=[C:13]([CH3:15])[N:14]=1)[C:10]([NH:2][OH:3])=[NH:11])[CH3:5]

Komponenten

4

Edukt 2

HCID 443297Hydroxyamine hydrochlorideHCID 685793492-(Ethyl-methyl-amino)-6-methyl-isonicotinonitrile

Produkt 1

HCID 178463716HCID 178463716, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel2×

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a solution of K tert butylate (574 mg, 5.11 mL) in methanol (10 mL), hydroxylamine hydrochloride (304 mg, 4.38 mmol) is added. To the stirred suspension, a solution of 2-(ethyl-methyl-amino)-6-methyl-isonicotinonitrile (256 mg, 1.46 mmol) in methanol (10 mL) is added and the resulting mixture is stirred at 60° C. for 15 h. The mixture is filtered, and the filtrate is concentrated. The residue is treated with 1 N aq. HCl, washed with DCM and then basified by adding 1 N aq. NaOH. The mixture is extracted three times with EA. The combined EA extracts are dried over MgSO4, filtered, concentrated and dried to give the title compound as a pale yellow oil; LC-MS: tR=0.45 min, [M+1]+=209.10; 1H NMR (D6-DMSO): δ 1.06 (t, J=6.5 Hz, 3H), 2.29 (s, 3H), 2.98 (s, 3H), 3.56 (q, J=6.3 Hz, 2H), 5.82 (s, 2H), 6.64 (s, 1H), 6.69 (s, 1H), 9.74 (s, 1H).

Aufarbeitung

  1. filtrationThe mixture is filtered
  2. concentrationthe filtrate is concentrated
  3. additionThe residue is treated with 1 N aq. HCl
  4. washwashed with DCM
  5. additionby adding 1 N aq. NaOH
  6. extractionThe mixture is extracted three times with EA
  7. dry with materialThe combined EA extracts are dried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customdried

Quellen und Nachweise

ORD-Eintrag
ord-33da42625afd41db8470cc547a067f8e
Quelldatensatz
uspto-grants-2013_11
Patentnummer
US08592460B2

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