Hydrochloric Acid → Hydrochloric Acid

HRID 244084Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 244084
[ClH:1].[CH:2]([C:4]1[CH:13]=[CH:12][C:7]([C:8]([O:10]C)=[O:9])=[CH:6][C:5]=1[N+:14]([O-])=O)=O.[C:17]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)(=O)[CH3:18].[OH-].[K+]>CCO.[Fe].O>[ClH:1].[C:20]1([C:17]2[CH:18]=[CH:2][C:4]3[C:5](=[CH:6][C:7]([C:8]([OH:10])=[O:9])=[CH:12][CH:13]=3)[N:14]=2)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.[ClH:1]

Komponenten

9

Edukt 4

HCID 313Hydrochloric AcidHCID 7410AcetophenoneHCID 14797Potassium HydroxideHCID 3457222Methyl 4-formyl-3-nitrobenzoate

Produkt 2

HCID 313Hydrochloric AcidHCID 159468702-Phenylquinoline-7-carboxylic acid hydrochloride

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23925IronKatalysatorHCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
95 °C

Versuchsvorschrift

Iron powder (21.05 g, 377 mmol), water (8 mL), and concentrated hydrochloric acid (0.63 mL, ˜7.5 mmol) were added consecutively to a solution of methyl 4-formyl-3-nitrobenzoate (8.04 g, 38.4 mmol) in EtOH (100 mL). The mixture was stirred at 95° C. for 1.5 h. Acetophenone (4.4 mL, 37.7 mmol) and solid KOH (6.344 g, 113 mmol) were then added with caution. This mixture was stirred at 95° C. for another 5 h. The inorganic solids were filtered off when still warm and the filtrate was acidified to pH=˜1.0 with 4 N HCl (aq). The solvents were removed and water (10 mL) was added. The product was extracted into THF (100 mL×3), dried over MgSO4, filtered, concentrated to afford the desired product as HCl salt; 1H-NMR (CD3OD, 400 MHz) δ 7.73-7.80 (m, 3H), 8.17-8.20 (m, 2H), 8.40-8.48 (m, 3H), 9.02 (d, J=0.8 Hz, 1H), 9.17 (d, J=8.8 Hz, 1H). MS (ES+): m/z 250 [MH+]. HPLC: tR=3.18 min (OpenLynx, polar—5 min).

Aufarbeitung

  1. stirringThis mixture was stirred at 95° C. for another 5 h
  2. filtrationThe inorganic solids were filtered off when
  3. temperaturestill warm
  4. customThe solvents were removed
  5. additionwater (10 mL) was added
  6. extractionThe product was extracted into THF (100 mL×3)
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-63293e1f8d8141cdb2921e4eb09c1df8
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08653268B2

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