Stannous Chloride → 2-amino-5-fluoro-3-methylbenzoic acid

HRID 61267Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 61267
[F:1][C:2]1[CH:3]=[C:4]([CH3:14])[C:5]([N+:11]([O-])=O)=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].Cl[Sn]Cl.C([O-])(O)=O.[Na+]>CCOC(C)=O>[NH2:11][C:5]1[C:4]([CH3:14])=[CH:3][C:2]([F:1])=[CH:10][C:6]=1[C:7]([OH:9])=[O:8]

Komponenten

5

Edukt 3

HCID 24479Stannous ChlorideHCID 516892Sodium BicarbonateHCID 534307765-Fluoro-3-methyl-2-nitrobenzoic acid

Produkt 1

HCID 289741642-amino-5-fluoro-3-methylbenzoic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

A mixture of 5-fluoro-3-methyl-2-nitrobenzoic acid (4.86 g, 24.42 mmol) and SnCl2 (16.5 g, 72.36 mmol) in EtOAc was heated at 70° C. overnight. After cooling at rt, the pH was adjusted to 7-8 with satd. aq. NaHCO3. The mixture was extracted with EtOAc, and the organic layer was washed with brine, filtered through diatomaceous earth, and dried over Na2SO4 to provide the title compound, which was used without further purification. ESI-MS (m/z): 170 [M+1]+.

Aufarbeitung

  1. temperatureAfter cooling at rt
  2. extractionThe mixture was extracted with EtOAc
  3. washthe organic layer was washed with brine
  4. filtrationfiltered through diatomaceous earth
  5. dry with materialdried over Na2SO4

Quellen und Nachweise

ORD-Eintrag
ord-fb9a274d3d724005b66f92d11eca9c4f
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09440982B2

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