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Hydroxyamine hydrochloride → HCID 178471206, Verbindung

HRID 2383316
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2383316
[C:1]([C:3]1[C:4]([CH3:28])=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]([CH2:13][CH2:14][CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])[N:8]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:7][CH2:6]2)#[N:2].Cl.[NH2:30][OH:31].C(=O)(O)[O-].[Na+]>C(O)C>[CH2:19]([O:18][C:16](=[O:17])[CH2:15][CH2:14][CH2:13][CH:9]1[C:10]2[C:5](=[C:4]([CH3:28])[C:3]([C:1]([NH:30][OH:31])=[NH:2])=[CH:12][CH:11]=2)[CH2:6][CH2:7][N:8]1[C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH3:20]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 443297Hydroxyamine hydrochloride4×HCID 516892Sodium Bicarbonate4×HCID 595910941,1-Dimethylethyl 6-cyano-1-[4-(ethyloxy)-4-oxobutyl]-5-methyl-3,4-dihydro-2(1H)-isoquinolinecarboxylate

Produkt 1

HCID 178471206HCID 178471206, VerbindungAusbeute 86,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702
Ethanol
Lösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A mixture of 1,1-dimethylethyl 6-cyano-1-[4-(ethyloxy)-4-oxobutyl]-5-methyl-3,4-dihydro-2(1H)-isoquinolinecarboxylate (Preparation 26; 533 mg, 1.38 mmol), hydroxylamine hydrochloride (575 mg, 8.27 mmol) and sodium bicarbonate (695 mg, 8.27 mmol) in ethanol (15 ml) was stirred at 80° C. for 32 h. More hydroxylamine hydrochloride and sodium bicarbonate (3 equivalent of each) were added, and heating was continued at 80° C. overnight. More hydroxylamine hydrochloride and sodium bicarbonate (3 equivalent of each) were added, and heating was continued at 80° C. for 5.5 h. More hydroxylamine hydrochloride and sodium bicarbonate (3 equivalent of each) were added, and heating was continued at 80° C. overnight. The mixture was cooled to room temperature and the solid was filtered off and washed with ethanol. The filtrate and washings were combined, most of the solvent removed, and the residue dissolved in ethyl acetate. The solution was washed with brine, dried over MgSO4 and concentrated in vacuo to give the title compound (500 mg) as a pale yellow foam.

Aufarbeitung

  1. temperatureheating
  2. waitwas continued at 80° C. overnight
  3. temperatureheating
  4. waitwas continued at 80° C. for 5.5 h
  5. temperatureheating
  6. waitwas continued at 80° C. overnight
  7. temperatureThe mixture was cooled to room temperature
  8. filtrationthe solid was filtered off
  9. washwashed with ethanol
  10. customremoved
  11. dissolutionthe residue dissolved in ethyl acetate
  12. washThe solution was washed with brine
  13. dry with materialdried over MgSO4
  14. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-f986d637a14f46a185fb6eafe5726ecc
Quelldatensatz
uspto-grants-2012_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08263620B2

Notizen zur Reaktion

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