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Sodium Hydroxide → 1-[7-benzyloxy-2-(hydroxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]-2-methylpropan-2-ol

HRID 598297
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 598297
Cl.C([O:5][CH2:6][C:7]([NH:9][C:10]1[CH:11]=[N:12][C:13]2[C:18]([C:19]=1[NH:20][CH2:21][C:22]([OH:25])([CH3:24])[CH3:23])=[CH:17][CH:16]=[C:15]([O:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[CH:14]=2)=O)(=O)C.[OH-].[Na+]>CO.O>[CH2:27]([O:26][C:15]1[CH:16]=[CH:17][C:18]2[C:19]3[N:20]([CH2:21][C:22]([CH3:24])([OH:25])[CH3:23])[C:7]([CH2:6][OH:5])=[N:9][C:10]=3[CH:11]=[N:12][C:13]=2[CH:14]=1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 2

HCID 14798Sodium HydroxideHCID 670510132-({7-Benzyloxy-4-[(2-hydroxy-2-methylpropyl)amino]quinolin-3-yl}amino)-2-oxoethyl acetate hydrochloride

Produkt 1

HCID 670509421-[7-benzyloxy-2-(hydroxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]-2-methylpropan-2-olAusbeute 97,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittel
HCID 962
Water
Lösungsmittel

Reaktionsbedingungen

Temperatur
55 °C

Versuchsvorschrift

A mixture of 2-({7-benzyloxy-4-[(2-hydroxy-2-methylpropyl)amino]quinolin-3-yl}amino)-2-oxoethyl acetate hydrochloride (54.0 g, 0.114 mol) in methanol (270 mL) was heated to 55° C., at which point a solution was obtained. A solution of sodium hydroxide (9.2 g, 0.23 mol) in water (90 mL) was then added over a period of five minutes while heating the reaction mixture at reflux. Following the addition, the addition funnel was rinsed with water (10 mL), and the reaction mixture was heated at reflux for one hour. The reaction mixture was then cooled to ˜0° C., and the solid product was isolated by filtration, washed with methanol, deionized water, and a small volume of acetone, and dried under vacuum at 50° C. to provide 42.1 g of 1-[7-benzyloxy-2-(hydroxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]-2-methylpropan-2-ol as an off-white solid.

Aufarbeitung

  1. customwas obtained
  2. temperaturewhile heating the reaction mixture
  3. temperatureat reflux
  4. additionthe addition
  5. washthe addition funnel was rinsed with water (10 mL)
  6. temperaturethe reaction mixture was heated
  7. temperatureat reflux for one hour
  8. temperatureThe reaction mixture was then cooled to ˜0° C.
  9. customthe solid product was isolated by filtration
  10. washwashed with methanol
  11. dry with materiala small volume of acetone, and dried under vacuum at 50° C.

Quellen und Nachweise

ORD-Eintrag
ord-7dc9583c76f34d2c9996dc46bc9f4377
Quelldatensatz
uspto-grants-2011_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07897597B2

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