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Sodium Hydroxide → 4-[3-Methyl-1-(8-methyl-quinolin-3-ylamino)-butyl]benzoic acid

HRID 2281146
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2281146
C([O:3][C:4](=[O:28])[C:5]1[CH:10]=[CH:9][C:8]([CH:11]([NH:16][C:17]2[CH:18]=[N:19][C:20]3[C:25]([CH:26]=2)=[CH:24][CH:23]=[CH:22][C:21]=3[CH3:27])[CH2:12][CH:13]([CH3:15])[CH3:14])=[CH:7][CH:6]=1)C.[OH-].[Na+]>C1COCC1.CO>[CH3:14][CH:13]([CH3:15])[CH2:12][CH:11]([C:8]1[CH:7]=[CH:6][C:5]([C:4]([OH:28])=[O:3])=[CH:10][CH:9]=1)[NH:16][C:17]1[CH:18]=[N:19][C:20]2[C:25]([CH:26]=1)=[CH:24][CH:23]=[CH:22][C:21]=2[CH3:27]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 2

HCID 14798Sodium HydroxideHCID 712395254-[3-Methyl-1-(8-methyl-quinoline-3-ylamino)-butyl]-benzoic acid ethyl ester

Produkt 1

HCID 712394574-[3-Methyl-1-(8-methyl-quinolin-3-ylamino)-butyl]benzoic acidAusbeute 79,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21899815MeOH tetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

A mixture of 4-[3-Methyl-1-(8-methyl-quinoline-3-ylamino)-butyl]-benzoic acid ethyl ester (62 mg, 0.16 mM) and 1N aqueous NaOH solution (0.413 mL, 0.413 mM) in THF-MeOH (1:1, 3.3 mL) was heated to 50° C. for 4 h. The reaction was cooled, concentrated to remove organic solvent. The aqueous solution was diluted with DCM (5 mL), acidified by 1N HCl solution to pH=3-4. The organic solution was separated and the aqueous solution was extracted with 10% i-PrOH-DCM (5×5 mL). The combined organic solution were dried (Na2SO4) and concentrated to give a yellow solid product (45.7 mg, 79%). 1H NMR (400 MHz, CD3OD) δ ppm 0.98 (d, J=6.44 Hz, 3 H) 1.03 (d, J=6.25 Hz, 3 H) 1.56-1.68 (m, 1 H) 1.73-1.93 (m, 2 H) 2.68 (d, 3 H) 4.60-4.68 (m, 1 H) 7.23-7.35 (m, 2 H) 7.38 (d, 1 H) 7.44 (d, 1 H) 7.48-7.61 (m, 2 H) 7.96 (d, 2 H) 8.53 (dd, 1 H), two protons (COOH and NH) were exchanged. This material will be used for the next step reaction without further work-up.

Aufarbeitung

  1. temperatureThe reaction was cooled
  2. concentrationconcentrated
  3. customto remove organic solvent
  4. additionThe aqueous solution was diluted with DCM (5 mL)
  5. customThe organic solution was separated
  6. extractionthe aqueous solution was extracted with 10% i-PrOH-DCM (5×5 mL)
  7. dry with materialThe combined organic solution were dried (Na2SO4)
  8. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-df846e72e7aa4cd3ae5386f1369f13ec
Quelldatensatz
uspto-grants-2015_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09139538B2

Notizen zur Reaktion

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