Sodium Hydroxide → 5-Bromoquinoline-8-carboxylic acid

HRID 2281001Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2281001
[Br:1][C:2]1[CH:11]=[CH:10][C:9]([CH:12]=[O:13])=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.[OH-:14].[Na+]>C1COCC1.[N+]([O-])([O-])=O.[Ag+]>[Br:1][C:2]1[CH:11]=[CH:10][C:9]([C:12]([OH:14])=[O:13])=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2

Komponenten

5

Edukt 2

HCID 14798Sodium HydroxideHCID 164142435-Bromoquinoline-8-carboxaldehyde

Produkt 1

HCID 592928605-Bromoquinoline-8-carboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24470Silver NitrateKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 5-Bromoquinoline-8-carbaldehyde (10 g, 0.039 mol) in THF (300 ml) was added aqueous NaOH (30 g) and followed by silver nitrate (10.79 g, 0.0635 mol) lot wise at RT for 10 min and this reaction mixture was stirred at RT for 30 min. The reaction completion was confirmed by TLC. After completion of reaction the reaction mixture was filtered. The black solid was wanded with THF, MeOH and DMF (50 ml each). (Note: Product was not soluble in any of these solvents!! The filtrate and washings were discarded). The black solid was dried to afford the title compound (crude −30 g). The crude product was as such taken for the next step. 1H NMR (DMSO-d6, 400 MHz): δ 8.92-8.91 (dd, J=4.12, 5.8 Hz, 1H), 8.49 (s, 1H), 8.46-8.44 (dd, J=8.56, 10.2 Hz, 1H), 7.83-7.81 (dd, J=7.6, Hz, 1H), 7.63-7.6 (dd, J=8.52, 12.68 Hz, 1H), 7.46-7.44 (d, J=7.6 Hz, 1H).

Aufarbeitung

  1. customAfter completion of reaction the reaction mixture
  2. filtrationwas filtered
  3. customThe black solid was dried

Quellen und Nachweise

ORD-Eintrag
ord-0f06ebd22dd54010b7544dcf446a2d56
Quelldatensatz
uspto-grants-2015_09
Patentnummer
US09139568B2

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