Sodium Hydroxide → HCID 44242581, Verbindung

HRID 1775960Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1775960
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:11][C:12]([O:14]CC)=[O:13])[C:6]1[CH2:17][N:18]([CH3:21])[CH2:19][CH2:20][C:5]2=1.[OH-].[Na+]>C1COCC1.O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:11][C:12]([OH:14])=[O:13])[C:6]1[CH2:17][N:18]([CH3:21])[CH2:19][CH2:20][C:5]2=1

Komponenten

5

Edukt 2

HCID 14798Sodium HydroxideHCID 57930381HCID 57930381, Verbindung

Produkt 1

HCID 44242581HCID 44242581, VerbindungAusbeute 21,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
75 °C

Versuchsvorschrift

Ethyl 2-(6-chloro-1,2,3,4-tetrahydro-2-methylpyrido[3,4-b]indol-9-yl)acetate (0.3 g, 2.9 mmol) in THF (10 mL) was added to a solution of sodium hydroxide (0.177 g, 2.9 mmol) in water (3 mL) and heated at 75° C. for 1 h. The progress of the reaction was monitored by TLC. After completion of the reaction, the solvent was removed; water (10 mL) was added to the residue and the aqueous layer was washed with ethyl acetate (2×10 mL). The pH of aqueous layer was adjusted to 2-3, and the aqueous layer was washed with ethyl acetate. The aqueous layer was evaporated, the residue was extracted with methanol, filtered, the filtrate was concentrated under reduced pressure to yield 2-(6-chloro-1,2,3,4-tetrahydro-2-methylpyrido[3,4-b]indol-9-yl)acetic acid (175 mg). 1H NMR (CD3OD): 7.50 (s, 1H) 7.30 (d, 1H), 7.10 (d, 1H), 5.1 (d, 1H), 5.0 (d, 1H), 4.4 (s, 2H), 4.2 (m, 1H), 4.0 (m, 1H), 3.4 (s, 3H), 3.2 (m, 2H).

Aufarbeitung

  1. customAfter completion of the reaction
  2. customthe solvent was removed
  3. additionwater (10 mL) was added to the residue
  4. washthe aqueous layer was washed with ethyl acetate (2×10 mL)
  5. washthe aqueous layer was washed with ethyl acetate
  6. customThe aqueous layer was evaporated
  7. extractionthe residue was extracted with methanol
  8. filtrationfiltered
  9. concentrationthe filtrate was concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-d66e3aa2fcb040de9d3fcd39aeed533b
Quelldatensatz
uspto-grants-2016_02
Patentnummer
US09260429B2

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