Hydrochloric Acid → 4-Methylquinoline-6-carbonitrile hydrochloride

HRID 253074

Reaktionsgleichung

Reaktionsgleichung von HRID 253074
[NH2:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1.[Cl:10][C:11]1[C:12](=O)C(Cl)=C(Cl)[C:15](=O)[C:16]=1Cl.Cl.CC(C=C)=O>CCO.O1CCCC1>[ClH:10].[C:6]([C:5]1[CH:4]=[C:3]2[C:2](=[CH:9][CH:8]=1)[N:1]=[CH:12][CH:11]=[C:16]2[CH3:15])#[N:7]

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 6570Methyl vinyl ketoneHCID 8371ChloranilHCID 133964-Aminobenzonitrile

Produkt 1

HCID 668665514-Methylquinoline-6-carbonitrile hydrochlorideAusbeute 82,55 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittel2×HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
75 °C

Versuchsvorschrift

Add 95% ethanol (EtOH) (270 L, 9 vol.), 4-aminobenzonitrile (30.0 kg, 1 equiv) and 2,3,5,6-tetrachloro-2,5-cyclohexadiene-1,4-dione, (66.81 kg 1.07 equiv) to a 200 gallon reaction vessel equipped with nitrogen purge, condenser, thermocouple, and overhead agitation. Stir for 2-5 min, then add concentrated hydrochloric acid (HCl) (62.56 L, 3.0 equiv), then heat to 75° C. Dilute methyl vinylketone (33.06 L, 1.5 equiv) in 95% EtOH (30 L, 1 vol.) then add slowly to reaction mixture over 30 min. Monitor for reaction completion by high performance liquid chromatography (HPLC). Add tetrahydrofuran (THF) (11 vol., 330 L), at 75° C., then stir for 1 hour at 60° C. Cool to room temperature and stir for 1 additional hour. Filter on agitated filter/dryer, then rinse with THF (240 L, 8 volumes). Dry overnight under vacuum at 70° C. to give the title compound (42.9 kg, 82.55%).

Aufarbeitung

  1. customto a 200 gallon reaction vessel
  2. customequipped with nitrogen
  3. custompurge
  4. customMonitor for reaction completion by high performance liquid chromatography (HPLC)
  5. temperatureCool to room temperature
  6. stirringstir for 1 additional hour
  7. filtrationFilter
  8. stirringon agitated
  9. filtrationfilter/dryer
  10. washrinse with THF (240 L, 8 volumes)
  11. customDry overnight under vacuum at 70° C.

Quellen und Nachweise

ORD-Eintrag
ord-be82749e844544239a8c401e06537fe7
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07872020B2

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