Lithium Hydroxide → 1-Acetyl-6-bromo-1,2,3,4-tetrahydroquinoline-2-carboxylic acid

HRID 1852604Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1852604
C[O:2][C:3]([CH:5]1[CH2:14][CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[C:10]([Br:15])[CH:11]=2)[N:6]1[C:16](=[O:18])[CH3:17])=[O:4].[Li+].[OH-]>C1COCC1.CO.O>[C:16]([N:6]1[C:7]2[C:12](=[CH:11][C:10]([Br:15])=[CH:9][CH:8]=2)[CH2:13][CH2:14][CH:5]1[C:3]([OH:4])=[O:2])(=[O:18])[CH3:17]

Komponenten

4

Edukt 2

HCID 3939Lithium HydroxideHCID 596259921-Acetyl-6-bromo-1,2,3,4-tetrahydro-quinoline-2-carboxylic acid methyl ester

Produkt 1

HCID 596259471-Acetyl-6-bromo-1,2,3,4-tetrahydroquinoline-2-carboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21892291Methanol tetrahydrofuran waterLösungsmittel

Versuchsvorschrift

To a solution of compound 25b (116 mg, 0.37 mmol) in THF/MeOH/H2O (2/2/2 mL) was added LiOH (62 mg, 1.48 mmol). The reaction mixture was stirred at room temperature for 3 h. The resultant mixture was concentrated under reduced pressure, partitioned between CH2Cl2 and H2O, and the aqueous phase was brought to pH 5 by the addition of 2N HCl (aq). The organic phase was dried over Na2SO4, filtered, and concentrated under reduced pressure to give the crude compound 25c, which was used in the next step without further purification. LC/MS m/z 298.0 (M+H+), 300.0 (M+2H+).

Aufarbeitung

  1. concentrationThe resultant mixture was concentrated under reduced pressure
  2. custompartitioned between CH2Cl2 and H2O
  3. additionthe aqueous phase was brought to pH 5 by the addition of 2N HCl (aq)
  4. dry with materialThe organic phase was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-bfd12252029546f291072ad4974094ca
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08962607B2

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