Stannous Chloride → HCID 67451538, Verbindung

HRID 571092

Reaktionsgleichung

Reaktionsgleichung von HRID 571092
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([O:11][CH3:12])[CH:3]=1.[N:13]([O-])=O.[Na+].[Sn](Cl)[Cl:18]>Cl.O>[ClH:18].[CH3:12][O:11][C:4]1[CH:3]=[C:2]([NH:1][NH2:13])[CH:10]=[CH:9][C:5]=1[C:6]([OH:8])=[O:7]

Komponenten

6

Edukt 3

HCID 24479Stannous ChlorideHCID 755994-Amino-o-anisic acidHCID 23668193Sodium Nitrite

Produkt 1

HCID 67451538HCID 67451538, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 313Hydrochloric AcidLösungsmittel2×HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a suspension of 4-amino-2-methoxybenzoic acid (3.00 g, 18.0 mmol) in hydrochoric acid (1.0 M, 30 mL) at 0° C. was added a solution of sodium nitrite (1.28 g, 18.5 mmol) in water (5.0 mL) over 5 min. The reaction mixture was maintained at 0° C. for 5 hr and was then treated with tin(II) chloride (9.53 g, 50.3 mmol) in hydrochloric acid (1M, 60 mL) and warmed to RT for 64 hr. A thick precipitate formed which was isolated by filtration, washed with water (50 mL) and ether (15 mL) and dried in vacuo to afford 2-methoxy-4-hydrazinylbenzoic acid hydrochloride as a beige solid (1.05 g, 90% purity, 24%); Rt 0.17 min (Method 2); m/z 181 (M+H)+, (ES+). This material was used in the subsequent step without further purification.

Aufarbeitung

  1. temperaturewarmed to RT for 64 hr
  2. customA thick precipitate formed which
  3. customwas isolated by filtration
  4. washwashed with water (50 mL) and ether (15 mL)
  5. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-ac315b3b73a945a7bd623cb7712163ca
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09024041B2

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