Lithium Hydroxide → 2-Chloroquinoline-7-carboxylic acid

HRID 537190Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 537190
[Cl:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][C:6]([C:12]([O:14]CC)=[O:13])=[CH:7][CH:8]=2)[N:3]=1.[OH-].[Li+]>O1CCCC1>[Cl:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][C:6]([C:12]([OH:14])=[O:13])=[CH:7][CH:8]=2)[N:3]=1

Komponenten

4

Edukt 2

HCID 3939Lithium HydroxideHCID 72942632Ethyl 2-chloroquinoline-7-carboxylate

Produkt 1

HCID 337786142-Chloroquinoline-7-carboxylic acidAusbeute 92 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of ethyl 2-chloroquinoline-7-carboxylate (800 mg, 3.4 mmol) in tetrahydrofuran (10 mL) was added 1 N aqueous lithium hydroxide (7 mL, 7 mmol). The reaction was stirred at room temperature overnight. The reaction was concentrated and the residue was diluted with water and acidified with 1 N aqueous hydrochloric acid. The resulting precipitate was collected by filtration and dried under vacuum to give the title compound (648 mg, 92%) as a white powder. +ESI (M+H) 208.1; 1H NMR (400 MHz, DMSO-d6, δ): 13.43 (s, 1H), 8.53 (d, J=8.7 Hz, 1H), 8.44-8.45 (m, 1H), 8.14 (d, J=8.4 Hz, 1H), 8.07-8.11 (m, 1H), 7.70 (d, J=8.5 Hz, 1H).

Aufarbeitung

  1. concentrationThe reaction was concentrated
  2. additionthe residue was diluted with water
  3. filtrationThe resulting precipitate was collected by filtration
  4. customdried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-0940d47ee878466da718c9ca7d8b58b3
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08859773B2

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