Glycerol → 8-Bromo-6-quinolinecarboxylic acid

HRID 1455629Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1455629
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[Br:11].O[CH2:13][CH:14]([CH2:16]O)O.S(=O)(=O)(O)O.[Na+].[N+](C1C=C(S([O-])(=O)=O)C=CC=1)([O-])=O>>[Br:11][C:3]1[CH:4]=[C:5]([C:6]([OH:8])=[O:7])[CH:9]=[C:10]2[C:2]=1[N:1]=[CH:16][CH:14]=[CH:13]2

Komponenten

5

Edukt 4

HCID 753GlycerolHCID 1118Sulfuric AcidHCID 31389Sodium 3-nitrobenzenesulfonateHCID 2389354-Amino-3-bromobenzoic acid

Produkt 1

HCID 106584338-Bromo-6-quinolinecarboxylic acid

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

4-Amino-3-bromo-benzoic acid (1 eq) and glycerol (2.4 eq) was added to sulfuric acid (6.4M, reaction conc. 0.6M) at 0° C. After 15 min, the bath was removed and 3-nitro-phenylsulfonic acid sodium salt (1.3 eq) was added portionwise. The reaction mixture was heated gradually until exothermic reaction started (between 110-140° C.), the internal temperature was maintained below 170° C. for 1 h. The reaction mixture was cooled to 50° C. and poured slowly into NH4OH-ice (2:1). The title product isolated by filtration, dissolved in warm 5% NH4OH/MeOH and diluted with CH2Cl2. This solution was filtered through silica gel eluting with (NH4OH, MeOH, CH2Cl2, 3:30:70). The residue was stirred in EtOH and the title product isolated by filtration.

Aufarbeitung

  1. customthe bath was removed
  2. temperatureThe reaction mixture was heated gradually until exothermic reaction
  3. custom(between 110-140° C.)
  4. temperaturethe internal temperature was maintained below 170° C. for 1 h

Quellen und Nachweise

ORD-Eintrag
ord-4e9d1b4b731946d1bc42e47d3f728348
Quelldatensatz
uspto-grants-2009_01
Patentnummer
US07482456B2

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