4-Toluenesulfonyl chloride → 6-Carbomethoxy-8-chloro-5-methoxy-1,2,3,4-tetrahydroquinoline

HRID 2074008Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2074008
O[CH2:2][CH2:3][CH2:4][C:5]1[C:6]([O:17][CH3:18])=[C:7]([CH:12]=[C:13]([Cl:16])[C:14]=1[NH2:15])[C:8]([O:10][CH3:11])=[O:9].C(N(CC)CC)C.S(Cl)(C1C=CC(C)=CC=1)(=O)=O>C(Cl)Cl.C1(C)C=CC=CC=1>[C:8]([C:7]1[C:6]([O:17][CH3:18])=[C:5]2[C:14](=[C:13]([Cl:16])[CH:12]=1)[NH:15][CH2:2][CH2:3][CH2:4]2)([O:10][CH3:11])=[O:9]

Komponenten

6

Edukt 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 14883230Methyl 3-(3-hydroxypropyl)-2-methoxy-4-amino-5-chlorobenzoate

Produkt 1

HCID 148832316-Carbomethoxy-8-chloro-5-methoxy-1,2,3,4-tetrahydroquinoline

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1140TolueneLösungsmittelHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

A mixture of the compound of step 4 above (1.4 g), triethylamine (1 ml) and TsCl (1.1 g) in CH2Cl2 is stirred at 25° C. for three days. The mixture is washed with saturated aqueous NaHCO3 and evaporated affording a residue which is dissolved in toluene and refluxed for 21/2 hours. The toluene is evaporated and the residue is dissolved in CH2Cl2 and washed with saturated NaHCO3 (25 mls). The organic layer is dried, evaporated and the residue chromatographed on silica gel affording a gum which crystallizes from HexEt2O to give the desired product (M.P. 105°-108° C.).

Aufarbeitung

  1. washThe mixture is washed with saturated aqueous NaHCO3
  2. customevaporated
  3. customaffording a residue which
  4. temperaturerefluxed for 21/2 hours
  5. customThe toluene is evaporated
  6. dissolutionthe residue is dissolved in CH2Cl2
  7. washwashed with saturated NaHCO3 (25 mls)
  8. customThe organic layer is dried
  9. customevaporated
  10. customthe residue chromatographed on silica gel affording a gum which
  11. customcrystallizes from HexEt2O

Quellen und Nachweise

ORD-Eintrag
ord-9d754c7a06e14d3ba3914a8e7d266380
Quelldatensatz
uspto-grants-1990_04
Patentnummer
US04920219

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