Quinaldic Acid → 3-Benzyloxy-6-(2-propyloxy)quinoline-2-carboxylic acid

HRID 1744

Reaktionsgleichung

Reaktionsgleichung von HRID 1744
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:11]([OH:13])=[O:12].S([C:18]1[CH:24]=CC(C)=C[CH:19]=1)(O)(=O)=O.[CH2:25]([O:32]C(=O)CN)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.C1C=CC2N([OH:46])N=NC=2C=1.CCCCCCC.C(OCC)(=O)C>C(Cl)Cl>[CH2:25]([O:32][C:3]1[C:2]([C:11]([OH:13])=[O:12])=[N:1][C:10]2[C:5]([CH:4]=1)=[CH:6][C:7]([O:46][CH:18]([CH3:24])[CH3:19])=[CH:8][CH:9]=2)[C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1

Komponenten

6

Edukt 4

HCID 7124Quinaldic AcidHCID 757711-HydroxybenzotriazoleHCID 6451311O-benzylglycine toluene-p-sulphonateHCID 21899848Ethylacetate heptane

Produkt 1

HCID 537797313-Benzyloxy-6-(2-propyloxy)quinoline-2-carboxylic acidAusbeute 129,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

2.7 g (8 mmol) of the above quinolinecarboxylic acid were reacted with 2.7 g (8 mmol) of glycine benzyl ester tosylate, 4.4 ml (32 mmol) of NEM, 1.35 g (10 mmol) of HOBT and 3.6 g (8.8 mmol) of CMC in 300 ml of anhydrous methylene chloride at 20° C. for 24 hours, analogously to Example 25g). After working up and chromatography over silica gel with n-heptane/ethyl acetate (3:2), 3.5 g of oily product were obtained.

Quellen und Nachweise

ORD-Eintrag
ord-dd95acbc02174382a8fb617b567ae3bb
Quelldatensatz
uspto-grants-1998_03
Patentnummer
US05726305

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