Tetrahydrothiopyran-4-one → 10-amino-3,4-dihydro-7-methyl-1H-thiopyrano[4,3-b]quinoline

HRID 1195712

Reaktionsgleichung

Reaktionsgleichung von HRID 1195712
[CH3:1][C:2]1[CH:3]=[C:4]([NH2:10])[C:5](=[CH:8][CH:9]=1)[C:6]#[N:7].[S:11]1[CH2:16][CH2:15][C:14](=O)[CH2:13][CH2:12]1>[N+](C1C=CC=CC=1)([O-])=O>[NH2:7][C:6]1[C:5]2[CH:8]=[CH:9][C:2]([CH3:1])=[CH:3][C:4]=2[N:10]=[C:14]2[CH2:15][CH2:16][S:11][CH2:12][C:13]=12

Komponenten

4

Edukt 2

HCID 66173Tetrahydrothiopyran-4-oneHCID 28012762-Amino-4-methylbenzonitrile

Produkt 1

HCID 1458024610-amino-3,4-dihydro-7-methyl-1H-thiopyrano[4,3-b]quinolineAusbeute 61,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 7416NitrobenzeneLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

A mixture of 4-methylanthranilonitrile (4.46 g) and freshly fused zinc chloride (6.8 g) in 20 ml of nitrobenzene was heated at 50° C. for 1 hour. To this was added tetrahydrothiopyran-4-one (5.1 g) and the mixture was heated to 130° C. for 1.5 hours. After cooling, the zinc complex was filtered, rinsed with ethyl ether and partitioned between 2-butanone (MEK) and NH4OH. The aqueous phase was extracted with MEK and the organics were washed with water and dried (saturated NaCl, MgSO4). This was concentrated to give 4.76 g of an off-white powder, m.p. 239°-245° C. d., which was recrystallized from ethyl acetate to give 2.95 g of an off-white powder, m.p. 243°-246° C. d.

Aufarbeitung

  1. temperaturethe mixture was heated to 130° C. for 1.5 hours
  2. temperatureAfter cooling
  3. filtrationthe zinc complex was filtered
  4. washrinsed with ethyl ether
  5. custompartitioned between 2-butanone (MEK) and NH4OH
  6. extractionThe aqueous phase was extracted with MEK
  7. washthe organics were washed with water
  8. dry with materialdried (saturated NaCl, MgSO4)
  9. concentrationThis was concentrated

Quellen und Nachweise

ORD-Eintrag
ord-bb49df6ea1974296b5c3a13bcc2deaf1
Quelldatensatz
uspto-grants-1992_05
Patentnummer
US05112830

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