Diisopropylethylamine → 4-chloro-7-methoxy-N,N-dimethylquinoline-6-carboxamide

HRID 387939Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 387939
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7]([Cl:13])=[CH:8][CH:9]=[N:10]2)=[CH:5][C:4]=1[C:14](Cl)=[O:15].COC1C=[C:27]2C(C(=O)C=[CH:25][NH:26]2)=CC=1C(O)=O.C(N(C(C)C)CC)(C)C.O1CCCC1.CNC>O1CCCC1.O>[CH3:25][N:26]([CH3:27])[C:14]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][C:3]=1[O:2][CH3:1])[N:10]=[CH:9][CH:8]=[C:7]2[Cl:13])=[O:15]

Komponenten

7

Edukt 4

HCID 81531DiisopropylethylamineHCID 22320367Dimethylamine tetrahydrofuranHCID 229364397-Methoxy-4-oxo-1,4-dihydroquinoline-6-carboxylic acidHCID 229365757-Methoxy-4-chloro-quinoline-6-carbonyl chloride

Produkt 1

HCID 589313634-chloro-7-methoxy-N,N-dimethylquinoline-6-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

After dissolving 7-methoxy-4-chloro-quinoline-6-carbonyl chloride synthesized by the method of Production Example 152-2 from 7-methoxy-4-oxo-1,4-dihydroquinoline-6-carboxylic acid (1.0 g) in tetrahydrofuran (60 ml), the solution was cooled to 0° C. Diisopropylethylamine (1.6 ml) and a 2.0 M dimethylamine tetrahydrofuran solution (3 ml) were added and the mixture was stirred overnight at room temperature. Water was added, extraction was performed 3 times with ethyl acetate, and the organic layers were combined, washed with water and saturated saline, dried over sodium sulfate and then dried under reduced pressure to obtain the title compound (933 mg).

Aufarbeitung

  1. extractionextraction
  2. washwashed with water and saturated saline
  3. dry with materialdried over sodium sulfate
  4. customdried under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-20a45e5f3f5b4017b65ccd6a4a1d1d8b
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08372981B2

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