Acetonitrile → 8-(2-Chloroethoxy)-7-methoxy-4-oxo-1,4-dihydrobenzo[g]quinoline-3-carbonitrile

HRID 989357Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 989357
C([Li])CCC.[C:6](#[N:8])[CH3:7].[Cl:9][CH2:10][CH2:11][O:12][C:13]1[CH:14]=[C:15]2[C:20](=[CH:21][C:22]=1[O:23][CH3:24])[CH:19]=[C:18]([C:25]([O:27]CC)=O)[C:17](/[N:30]=[CH:31]/N(C)C)=[CH:16]2.ClCCOC1C=C2C(C=C(/N=C/N(C)C)C(C(OCC)=O)=C2)=CC=1OC>O1CCCC1>[Cl:9][CH2:10][CH2:11][O:12][C:13]1[C:22]([O:23][CH3:24])=[CH:21][C:20]2[CH:19]=[C:18]3[C:17](=[CH:16][C:15]=2[CH:14]=1)[NH:30][CH:31]=[C:7]([C:6]#[N:8])[C:25]3=[O:27]

Komponenten

6

Edukt 4

HCID 6342AcetonitrileHCID 178418339ButyllithiumHCID 178468532HCID 178468532, VerbindungHCID 178468534HCID 178468534, Verbindung

Produkt 1

HCID 115372188-(2-Chloroethoxy)-7-methoxy-4-oxo-1,4-dihydrobenzo[g]quinoline-3-carbonitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel3×

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

To 2.5 mL of dry tetrahydrofuran at −78° C. is added 1.8 mL of 2.5 M n-butyllithium (4.4 mmol). Then 0.24 mL of dry acetonitrile in 4.5 mL of dry tetrahydrofuran is added dropwise over 10 minutes. This is stirred and additional 15 minutes at −78° C., then the ethyl 6-(2-chloroethoxy)-3-{[(E)-(dimethylamino)methylidene]-amino}-7-methoxy-2-naphthoate and ethyl 7-(2-chloroethoxy)-3-{[(E)-(dimethylamino)methylidene]amino}-6-methoxy-2-naphthoate (1:1 mixture) is dissolved in 3 mL of tetrahydrofuran and added dropwise over 15 minutes. The reaction mixture is stirred for 30 minutes at −78° C., then quenched with 0.57 mL of glacial acetic acid, and warmed to room temperature. To the yellow mixture is added 10 mL of water. The solids are filtered, washed with water and dried to give 0.502 g of 8-(2-chloroethoxy)-7-methoxy-4-oxo-1,4-dihydrobenzo[g]quinoline-3-carbonitrile and 7-(2-chloroethoxy)-8-methoxy-4-oxo-1,4-dihydrobenzo[g]quinoline-3-carbonitrile (1:1 mixture) as a yellow green solid (76%), m.p. 260-73° C. dec.

Aufarbeitung

  1. additionadded dropwise over 15 minutes
  2. stirringThe reaction mixture is stirred for 30 minutes at −78° C.
  3. customquenched with 0.57 mL of glacial acetic acid
  4. temperaturewarmed to room temperature
  5. additionTo the yellow mixture is added 10 mL of water
  6. filtrationThe solids are filtered
  7. washwashed with water
  8. customdried

Quellen und Nachweise

ORD-Eintrag
ord-fe68b54451314a209a90848340f916c0
Quelldatensatz
uspto-grants-2003_10
Patentnummer
US06638929B2

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