Sodium Acetate → Isopropyl 2-amino-1,4-dihydro-5-cyano-6-methyl-4-(3-phenyl-quinolin-5-yl)-pyridine-3-carboxylate

HRID 483606Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 483606
[C:1]1([C:7]2[CH:8]=[N:9][C:10]3[CH:11]=[CH:12][CH:13]=[C:14]([CH:17]=O)[C:15]=3[CH:16]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:19]/[C:20](/[CH3:24])=[CH:21]\[C:22]#[N:23].Cl.[C:26]([CH2:29][C:30]([O:32][CH:33]([CH3:35])[CH3:34])=[O:31])(=N)[NH2:27].C([O-])(=O)C.[Na+]>C(O)(C)C>[NH2:27][C:26]1[NH:19][C:20]([CH3:24])=[C:21]([C:22]#[N:23])[CH:17]([C:14]2[CH:13]=[CH:12][CH:11]=[C:10]3[C:15]=2[CH:16]=[C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH:8]=[N:9]3)[C:29]=1[C:30]([O:32][CH:33]([CH3:35])[CH3:34])=[O:31]

Komponenten

6

Edukt 4

HCID 517045Sodium AcetateHCID 5325263(2Z)-3-Amino-2-butenenitrileHCID 12391081Isopropyl amidinoacetate hydrochlorideHCID 151703323-Phenylquinoline-5-carbaldehyde

Produkt 1

HCID 9823672Isopropyl 2-amino-1,4-dihydro-5-cyano-6-methyl-4-(3-phenyl-quinolin-5-yl)-pyridine-3-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3776IsopropanolLösungsmittel

Versuchsvorschrift

4.66 g (20 mmol) of 3-phenyl-quinoline-5-aldehyde are boiled in 40 ml of isopropanol with 1.64 g (20 mmol) of 3-aminocrotononitrile, 3.6 g (20 mmol) of isopropyl amidinoacetate hydrochloride and 1.64 g (20 mmol) of sodium acetate for 20 hours. The mixture is concentrated, the residue is taken up in ethyl acetate/water and the phases are separated. The organic phase is washed twice with water, dried and concentrated. The reaction mixture is separated over a silica gel column using methylene chloride/ethyl acetate mixtures. The desired fractions are collected and concentrated. The resulting evaporation residue is crystallised with acetonitrile and filtered off with suction 635 mg of colourless crystals of melting point 227°-229° C. are obtained.

Aufarbeitung

  1. concentrationThe mixture is concentrated
  2. customthe phases are separated
  3. washThe organic phase is washed twice with water
  4. customdried
  5. concentrationconcentrated
  6. customThe reaction mixture is separated over a silica gel column
  7. customThe desired fractions are collected
  8. concentrationconcentrated
  9. customThe resulting evaporation residue
  10. customis crystallised with acetonitrile
  11. filtrationfiltered off with suction 635 mg of colourless crystals of melting point 227°-229° C.
  12. customare obtained

Quellen und Nachweise

ORD-Eintrag
ord-47e2a0a05461448797a1febcbc753667
Quelldatensatz
uspto-grants-1993_07
Patentnummer
US05225558

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