Sodium bis(trimethylsilyl)amide → 7-chloro-3-(3,5-dimethylphenyl)-4-hydroxy-6-iodoquinolin-2(1H)-one

HRID 1858090Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1858090
C[O:2][C:3](=O)[C:4]1[CH:9]=[C:8]([I:10])[C:7]([Cl:11])=[CH:6][C:5]=1[NH:12][C:13](=[O:23])[CH2:14][C:15]1[CH:20]=[C:19]([CH3:21])[CH:18]=[C:17]([CH3:22])[CH:16]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Na+]>O1CCCC1>[Cl:11][C:7]1[CH:6]=[C:5]2[C:4]([C:3]([OH:2])=[C:14]([C:15]3[CH:20]=[C:19]([CH3:21])[CH:18]=[C:17]([CH3:22])[CH:16]=3)[C:13](=[O:23])[NH:12]2)=[CH:9][C:8]=1[I:10]

Komponenten

4

Edukt 2

HCID 2724254Sodium bis(trimethylsilyl)amideHCID 540909164-Chloro-2-[2-(3,5-dimethylphenyl)-acetylamino]-5-iodo-benzoic acid methyl ester

Produkt 1

HCID 547112397-chloro-3-(3,5-dimethylphenyl)-4-hydroxy-6-iodoquinolin-2(1H)-oneAusbeute 96,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 4-chloro-2-[2-(3,5-dimethylphenyl)-acetylamino]-5-iodo-benzoic acid methyl ester (EXAMPLE 4.1B, 10.9 g in 180 mL dry tetrahydrofuran) at 0° C. was added dropwise 59.5 mL of a 1 M solution of sodium bis(trimethylsilyl)amide in tetrahydrofuran and the mixture allowed to warm to room temperature. After 1.5 hours, the mixture was cooled to 0° C. and the reaction quenched by the addition of 400 mL ice:6N hydrochloric acid (1:1). This was stirred for 15 minutes then filtered to collect the solid product. The solids were washed with ice-water then cold acetonitrile and dried to give the title compound (9.8 g).

Aufarbeitung

  1. temperaturethe mixture was cooled to 0° C.
  2. customthe reaction quenched by the addition of 400 mL ice
  3. filtrationthen filtered
  4. customto collect the solid product
  5. washThe solids were washed with ice-water
  6. dry with materialcold acetonitrile and dried

Quellen und Nachweise

ORD-Eintrag
ord-329a57b13be64629b7654de506e5bf37
Quelldatensatz
uspto-grants-2000_11
Patentnummer
US06150352

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