Sulfuric Acid → Methyl 6-bromoquinoline-3-carboxylate

HRID 1894955Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1894955
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][C:6]([C:12]([OH:14])=[O:13])=[CH:5]2.S(=O)(=O)(O)O.[C:20](=O)(O)[O-].[Na+]>CO>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][C:6]([C:12]([O:14][CH3:20])=[O:13])=[CH:5]2

Komponenten

5

Edukt 3

HCID 1118Sulfuric AcidHCID 516892Sodium BicarbonateHCID 170395906-Bromoquinoline-3-carboxylic acid

Produkt 1

HCID 53465709Methyl 6-bromoquinoline-3-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
85 °C

Versuchsvorschrift

To a solution of 6-bromoquinoline-3-carboxylic acid (3 g, 11.9 mmol), in methanol (55 mL) was added sulfuric acid (0.32 mL, 6 mmol). The reaction was stirred at 85° C. for 96 h. The reaction was then cooled to room temperature and saturated sodium bicarbonate solution was added until pH=7. On neutralization, methyl 7-bromo-2-naphthoate precipitated as a solid which was collected by suction filtration (Int-1, 2.77 g, 97%). LC-MS: (FA) ES+ 266; 1H NMR (400 MHz, d6-DMSO) δ ppm 9.33 (d, J=2.1 Hz, 1H), 9.01 (d, J=2.1 Hz, 1H), 8.53 (t, J=1.3, 1.3 Hz, 1H), 8.07-8.01 (m, 2H), 3.95 (s, 3H).

Aufarbeitung

  1. temperatureThe reaction was then cooled to room temperature
  2. customOn neutralization, methyl 7-bromo-2-naphthoate precipitated as a solid which
  3. filtrationwas collected by suction filtration (Int-1, 2.77 g, 97%)

Quellen und Nachweise

ORD-Eintrag
ord-6a4fc7b24771433da36fa2f3d02e45b8
Quelldatensatz
uspto-grants-2013_08
Patentnummer
US08513421B2

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