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Sodium Hydroxide → 3-Amino-7-vinylquinoline-2-carboxylic acid

HRID 924385
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 924385
C(OC([NH:11][C:12]1[C:13]([C:23]([O:25]CC)=[O:24])=[N:14][C:15]2[C:20]([CH:21]=1)=[CH:19][CH:18]=[C:17](Br)[CH:16]=2)=O)C1C=CC=CC=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].[CH3:36][C:37]1(C)C(C)(C)OB(C=C)O1.[OH-].[Na+]>C1(P(C2CCCCC2)C2C=CC=CC=2C2C(C(C)C)=CC(C(C)C)=CC=2C(C)C)CCCCC1.NC1C=CC=CC=1C1C=CC=CC=1[Pd]Cl.O.O1CCOCC1>[NH2:11][C:12]1[C:13]([C:23]([OH:25])=[O:24])=[N:14][C:15]2[C:20]([CH:21]=1)=[CH:19][CH:18]=[C:17]([CH:36]=[CH2:37])[CH:16]=2
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Komponenten

8

Edukt 4

HCID 14798Sodium HydroxideHCID 62657Potassium Phosphate, TribasicHCID 52330122-Ethenyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 86726857Ethyl 3-(((benzyloxy)carbonyl)amino)-7-bromoquinoline-2-carboxylate

Produkt 1

HCID 867268673-Amino-7-vinylquinoline-2-carboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178439015HCID 178439015, VerbindungKatalysator
HCID 962WaterLösungsmittel
HCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

Ethyl 3-{[(benzyloxy)carbonyl]amino}-7-bromoquinoline-2-carboxylate (1.50 g, 3.49 mmol), K3PO4 (1.48 g, 6.97 mmol), 1,4-dioxane (45 mL), water (7.5 mL) and 4,4,5,5-tetramethyl-2-vinyl-1,3,2-dioxaborolane (0.80 g, 5.2 mmol) were added to a flask. The reaction mixture was purged with nitrogen for 10 min., then dicyclohexyl(2′,4′,6′-triisopropylbiphenyl-2-yl)phosphine-(2′-aminobiphenyl-2-yl)(chloro)palladium (1:1) (0.18 g, 0.23 mmol) was added. The flask was then sealed and the reaction mixture was heated at 80° C. for 1 h, then allowed to cool to room temperature. After the reaction mixture was allowed to cool, aq. NaOH (2.5 M; 45 mL) was added, the resulting cloudy mixture was then heated at 95° C. for 3 h, and then allowed to cool. The crude product formed as a precipitate, which was collected by vacuum filtration and used in the next step without further purification. LCMS calc. for C12H11N2O2 (M+H)+: m/z=215.2. Found: 215.0.

Aufarbeitung

  1. customThe reaction mixture was purged with nitrogen for 10 min.
  2. customThe flask was then sealed
  3. temperatureto cool to room temperature
  4. temperatureto cool
  5. temperaturethe resulting cloudy mixture was then heated at 95° C. for 3 h
  6. temperatureto cool

Quellen und Nachweise

ORD-Eintrag
ord-319ef15571604013af1824a22eb5121c
Quelldatensatz
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09278950B2

Notizen zur Reaktion

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