Quinoline → 2-Amino-4-hydroxy-3-methylbenzonitrile

HRID 531383Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 531383
[CH2:1]([N:8]1C(=O)C2=CC=CC=C2C1=O)CCCCC=C.[OH-:19].[Na+].[N:21]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH:24]=CC=1>>[NH2:21][C:30]1[C:25]([CH3:24])=[C:26]([OH:19])[CH:27]=[CH:28][C:29]=1[C:1]#[N:8]

Komponenten

4

Edukt 3

HCID 7047QuinolineHCID 14798Sodium HydroxideHCID 53236045N-(hept-6-enyl)phthalimide

Produkt 1

HCID 134647162-Amino-4-hydroxy-3-methylbenzonitrileAusbeute 82 %

Reaktionsbedingungen

Temperatur
170 °C

Versuchsvorschrift

A mixture of compound 75 (19 g, 0.1 mol) in quinoline (50 mL) was heated to 170° C. for 2 h (until effervescence ceased). The reaction mixture was cooled to RT and aqueous NaOH solution was added (1M, 500 mL) followed by pet. ether (500 mL). The reaction mixture was stirred for 15 min and the aqueous layer was separated. The aqueous layer was further washed with pet. ether (2×300 mL) to remove quinoline completely. The aqueous layer was acidified with 1.5N HCl to pH=5, the solid was filtered off and dried under vacuum. The obtained solid was further washed with 5% ethyl acetate in pet. ether to give pure title compound (12 g, 82%).

Aufarbeitung

  1. temperatureThe reaction mixture was cooled to RT
  2. customthe aqueous layer was separated
  3. washThe aqueous layer was further washed with pet. ether (2×300 mL)
  4. customto remove quinoline completely
  5. filtrationthe solid was filtered off
  6. customdried under vacuum
  7. washThe obtained solid was further washed with 5% ethyl acetate in pet. ether

Quellen und Nachweise

ORD-Eintrag
ord-c9a0e766973a40a0a07e0d9f7feb87c4
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09353103B2

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