Hydrochloric Acid → HCID 57681003, Verbindung

HRID 244210

Reaktionsgleichung

Reaktionsgleichung von HRID 244210
Cl.[Cl:2][C:3]1[CH:10]=[CH:9][C:6]([CH:7]=O)=[C:5]([N+:11]([O-])=O)[CH:4]=1.[N:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[C:20](=O)[CH3:21].[OH-].[K+]>CCO.ClCCl.[Fe].O>[Cl:2][C:3]1[CH:4]=[C:5]2[C:6]([CH:7]=[CH:21][C:20]([C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][N:14]=3)=[N:11]2)=[CH:9][CH:10]=1

Komponenten

9

Edukt 4

HCID 313Hydrochloric Acid2×HCID 142862-AcetylpyridineHCID 14797Potassium HydroxideHCID 796744-Chloro-2-nitrobenzaldehyde

Produkt 1

HCID 57681003HCID 57681003, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 23925IronKatalysatorHCID 702EthanolLösungsmittelHCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
95 °C

Versuchsvorschrift

Iron powder (167 g, 2990 mmol), water (60 mL), and concentrated hydrochloric acid (3 mL, ˜36 mmol) were added consecutively to a solution of 4-chloro-2-nitrobenzaldehyde (55.7 g, 300 mmol) in EtOH (600 mL). After stirred (mechanically) at 95° C. for 10 min, another aliquot of concentrated hydrochloric acid (2 mL, ˜24 mmol) was added. Stirring was continued at 95° C. for another 80 min. 1-Pyridin-2-ylethanone (33 mL, 294.1 mmol) and solid KOH (50.5 g, 900 mmol) were then added in portions with caution. The resulting mixture was stirred at 95° C. for 4 h. After cooled to rt, the reaction was diluted with dichloromethane (500 mL) and filtered through a Celite pad. The filtrate was concentrated to approximately 100 mL. The desired precipitated product was collected by filtration; 1H-NMR (CDCl3, 400 MHz) δ 7.37-7.40 (m, 1H), 7.51 (dd, J=2.0, 8.8 Hz, 1H), 7.79 (d, J=8.4 Hz, 1H), 7.89 (dt, J=1.6, 8.0 Hz, 1H), 8.19 (s, 1H), 8.26 (d, J=8.8 Hz, 1H), 8.57 (d, J=8.8 Hz, 1H), 8.64 (d, J=8.4 Hz, 1H), 8.74-8.75 (m, 1H); MS (ES+): m/z 241 (MH+, 35Cl), 243 (MH+, 37Cl); HPLC: tR=3.95 min (OpenLynx, polar—5 min).

Aufarbeitung

  1. stirringStirring
  2. waitwas continued at 95° C. for another 80 min
  3. stirringThe resulting mixture was stirred at 95° C. for 4 h
  4. temperatureAfter cooled to rt
  5. filtrationfiltered through a Celite pad
  6. concentrationThe filtrate was concentrated to approximately 100 mL
  7. customThe desired precipitated product
  8. filtrationwas collected by filtration
  9. customHPLC: tR=3.95 min (OpenLynx, polar—5 min)

Quellen und Nachweise

ORD-Eintrag
ord-51ec2ddda63045148ee1b440be930854
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08653268B2

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