Sodium bis(trimethylsilyl)amide → 7-chloro-4-hydroxy-6-nitro-3-(thiophen-2-yl)quinolin-2(1H)-one

HRID 1858166Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1858166
CO[C:3](=[O:23])[C:4]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[C:7]([Cl:13])=[CH:6][C:5]=1[NH:14][C:15](=[O:22])[CH2:16][C:17]1[S:18][CH:19]=[CH:20][CH:21]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Na+]>O1CCCC1>[Cl:13][C:7]1[CH:6]=[C:5]2[C:4]([C:3]([OH:23])=[C:16]([C:17]3[S:18][CH:19]=[CH:20][CH:21]=3)[C:15](=[O:22])[NH:14]2)=[CH:9][C:8]=1[N+:10]([O-:12])=[O:11]

Komponenten

4

Edukt 2

HCID 2724254Sodium bis(trimethylsilyl)amideHCID 54055967Methyl 4-chloro-5-nitro-2-(2-(thiophen-2-yl)acetamido)benzoate

Produkt 1

HCID 547119717-chloro-4-hydroxy-6-nitro-3-(thiophen-2-yl)quinolin-2(1H)-oneAusbeute 66,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 4-chloro-5-nitro-2-(2-thiophen-2-yl-acetylamino)-benzoic acid methyl ester (130 mg in 4.0 mL dry tetrahydrofuran) at 0° C. was added dropwise a solution of sodium bis(trimethylsilyl)amide (0.92 mL of a 1.0M solution in tetrahydrofuran) and the mixture warmed to room temperature. After 3 hours, the reaction was quenched by the addition of 6N hydrochloric acid. The slurry was stirred for 10 minutes then filtered and washed with ice cold acetonitrile. The residue was dried in vacuo to give the title compound (79 mg).

Aufarbeitung

  1. customthe reaction was quenched by the addition of 6N hydrochloric acid
  2. filtrationthen filtered
  3. washwashed with ice cold acetonitrile
  4. customThe residue was dried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-77b4e7fb5cd449d6b74d78aa7113f971
Quelldatensatz
uspto-grants-2000_11
Patentnummer
US06150522

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