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

HRID 1275590Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1275590
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-6df337286c3d400c9d166282ebbb73e8
Quelldatensatz
uspto-grants-2000_12
Patentnummer
US06162813

Notizen zur Reaktion

Wird geladen…