Salicylic Acid → 3-Chloro-N-(4-pyridinyl)-1H-indol-1-amine salicylate

HRID 1955671Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1955671
[Cl:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]([NH2:11])[CH:3]=1.Cl.Cl[C:14]1[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=1.[C:20]([OH:29])(=[O:28])[C:21]1[C:22](=[CH:24][CH:25]=[CH:26][CH:27]=1)[OH:23]>CN1CCCC1=O.C(OCC)(=O)C>[C:20]([OH:29])(=[O:28])[C:21]1[C:22](=[CH:24][CH:25]=[CH:26][CH:27]=1)[OH:23].[Cl:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]([NH:11][C:14]2[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=2)[CH:3]=1

Komponenten

6

Edukt 3

HCID 338Salicylic AcidHCID 818524-Chloropyridine hydrochlorideHCID 9964198N-Amino-3-chloro-1H-indole

Produkt 1

HCID 700281183-Chloro-N-(4-pyridinyl)-1H-indol-1-amine salicylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8857Ethyl AcetateLösungsmittelHCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

A suspension of crude 3-chloro-1H-indol-1-amine (65.5 g) and 4-chloropyridine hydrochloride (45 g) in 1-methyl-2-pyrrolidinone (250 ml) was stirred at 60° C. for eight hours. The cooled reaction mixture was quenched into 5% aqueous sodium hydroxide, extracted into toluene, dried and concentrated to give an oil. A portion of this oil was dissolved in ethyl acetate. Salicylic acid (1.2 eq) was added to precipitate the salt. The solid was collected at room temperature and dried. This solid was recrystallized with a charcoal treatment from methanol and oven dried (75° C., house vacuum) overnight to yield 10.9 g of the title compound as a solid, m.p. 185°-186° C. (dec.).

Aufarbeitung

  1. customThe cooled reaction mixture
  2. customwas quenched into 5% aqueous sodium hydroxide
  3. extractionextracted into toluene
  4. customdried
  5. concentrationconcentrated
  6. customto give an oil
  7. customto precipitate the salt
  8. customThe solid was collected at room temperature
  9. customdried
  10. customThis solid was recrystallized with a charcoal treatment from methanol and oven
  11. customdried (75° C., house vacuum) overnight

Quellen und Nachweise

ORD-Eintrag
ord-9c978422951b49fc94b95ff9711b848a
Quelldatensatz
uspto-grants-1998_07
Patentnummer
US05776955

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