Hydrochloric Acid → HCID 59726101, Verbindung

HRID 336428Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 336428
[Cl:1][C:2]1[CH:10]=[C:9]([Cl:11])[C:5]([C:6]([OH:8])=[O:7])=[C:4]([N+:12]([O-:14])=[O:13])[C:3]=1[OH:15].[C:16]([O-])([O-])=O.[K+].[K+].IC.Cl>CN(C=O)C.O>[Cl:1][C:2]1[CH:10]=[C:9]([Cl:11])[C:5]([C:6]([OH:8])=[O:7])=[C:4]([N+:12]([O-:14])=[O:13])[C:3]=1[O:15][CH3:16]

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 106584324,6-Dichloro-3-hydroxy-2-nitrobenzoic acid

Produkt 1

HCID 59726101HCID 59726101, VerbindungAusbeute 88,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a solution of acid 1-6 (0.88 g, 3.5 mmol) in DMF (8 mL) was added K2CO3 (1.44 g, 10 mmol) followed by iodomethane (0.43 mL, 6.95 mmol). The reaction was heated to 60° C. for 17 h then DMF was removed under reduced pressure to give an orange gum. H2O (20 mL) was added and the solution was acidified to pH 1 with a 10% HCl solution. The aqueous solution was then extracted with EtOAc (30 mL) and washed with H2O and brine. After drying over Na2SO4 the reaction was filtered and concentrated to afford 1-7 as an orange gum (0.82 g, 88% yield). 1H NMR (400 MHz, CDCl3) δ 3.94 (s, 3H), 7.69 (s, 1H), 10.85 (br s, 1H).

Aufarbeitung

  1. customDMF was removed under reduced pressure
  2. customto give an orange gum
  3. extractionThe aqueous solution was then extracted with EtOAc (30 mL)
  4. washwashed with H2O and brine
  5. dry with materialAfter drying over Na2SO4 the reaction
  6. filtrationwas filtered
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-6cbfdab896644684a77bab73235d9c01
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08889695B2

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