Sodium borohydride → 4-(3-chloro-phenyl)-6-[(5-chloro-thiophen-2-yl)-hydroxy-methyl]-1-methyl-1H-quinolin-2-one

HRID 50181Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 50181
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([C:18]([C:20]4[S:21][C:22]([Cl:25])=[CH:23][CH:24]=4)=[O:19])[CH:16]=3)[N:11]([CH3:26])[C:10](=[O:27])[CH:9]=2)[CH:5]=[CH:6][CH:7]=1.[BH4-].[Na+]>CO>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([CH:18]([C:20]4[S:21][C:22]([Cl:25])=[CH:23][CH:24]=4)[OH:19])[CH:16]=3)[N:11]([CH3:26])[C:10](=[O:27])[CH:9]=2)[CH:5]=[CH:6][CH:7]=1

Komponenten

4

Edukt 2

HCID 4311764Sodium borohydride2×HCID 224654034-(3-Chloro-phenyl)-6-(5-chloro-thiophene-2-carbonyl)-1-methyl-1h-quinolin-2-one

Produkt 1

HCID 224654214-(3-chloro-phenyl)-6-[(5-chloro-thiophen-2-yl)-hydroxy-methyl]-1-methyl-1H-quinolin-2-oneAusbeute 78,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a suspension of 4-(3-chloro-phenyl)-6-(5-chloro-thiophene-2-carbonyl)-1-methyl-1H-quinolin-2-one (58 mg, 0.154 mmol) in MeOH (1 ml) was added sodium borohydride as solid (NaBH4, 7 mg, 0.185 mmol) at 0° C. The reaction mixture was stirred at 0° C. for one hour after which time it was partitioned between chloroform and water. The organic layer was washed with brine, dried over MgSO4 and concentrated under vacuum to give an off-white solid (49 mg, 78.5% yield).

Aufarbeitung

  1. customwas partitioned between chloroform and water
  2. washThe organic layer was washed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-9b3174060c9648ef9c859e063a499b1e
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06710209B2

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