Hydrochloric Acid → 5-(3-Chloro-phenyl)-3,3-diethyl-1,3-dihydro-indol-2-one

HRID 990643

Reaktionsgleichung

Reaktionsgleichung von HRID 990643
[CH2:1]([C:3]1[C:4](=[O:12])[N:5]=[C:6]2[C:11]=1[CH:10]=[CH:9][CH:8]=[CH:7]2)[CH3:2].[CH2:13]([Li])[CH2:14][CH2:15][CH3:16].CN(C)[CH2:20][CH2:21]N(C)C.I[CH2:27][CH3:28].[ClH:29]>C1COCC1>[Cl:29][C:14]1[CH:15]=[C:16]([C:9]2[CH:10]=[C:11]3[C:6](=[CH:7][CH:8]=2)[NH:5][C:4](=[O:12])[C:3]3([CH2:20][CH3:21])[CH2:1][CH3:2])[CH:27]=[CH:28][CH:13]=1

Komponenten

7

Edukt 5

HCID 313Hydrochloric AcidHCID 6340IodoethaneHCID 8037N,N,N',N'-TetramethylethylenediamineHCID 219862793-Ethylindol-2-oneHCID 178418339Butyllithium

Produkt 1

HCID 99482465-(3-Chloro-phenyl)-3,3-diethyl-1,3-dihydro-indol-2-oneAusbeute 45 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of 3-ethylindol-2-one (16 g, 0.1 mol) in dry THF (200 ml) under N2 was cooled to −25° C. and treated drop wise with n-butyllithium (2.5M in hexanes, 80 ml, 0.2 mol). To the resulting solution was added N,N,N′,N′-tetramethylethylenediamine (30 ml, 0.2 mol). After 30 min. iodoethane (8 ml, 0.1 mol) was added and the reaction rnixture was allowed to warm to RT and stirred over night. The reaction mixture was poured into an aqueous HCl solution, extracted with EtOAc (2×) and the combined organic layers were washed with dil. HCl, water, brine, dried (MgSO4) and concentrated. The residual oil was triturated with hexane to afford the title product (9 g, 45%), mp. 156-159° C. 1H NMR (DMSO-d6) δ 10.44 (s, 1H), 7.70-7.69 (t, 1H), 7.62-7.59 (m, 1H), 7.58 (d, 1H J=1.7 Hz), 7.53-7.50 (m, 1H), 7.45-7.41 (t, 1H), 7.36-7.35 (m, 1H), 7.34-7.33 (m, 1H), 6.91-6.89 (d, 1H J=8.2 Hz), 1.87-1.80 (m, 2H), 1.77-1.70 (m, 2H), 0.54-0.50 (t, 6H); MS (+ESI) m/z 190 (M+H).

Aufarbeitung

  1. extractionextracted with EtOAc (2×)
  2. washthe combined organic layers were washed with dil. HCl, water, brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customThe residual oil was triturated with hexane

Quellen und Nachweise

ORD-Eintrag
ord-a0dc37b3a01e44b29e9052bcbabeb776
Quelldatensatz
uspto-grants-2002_10
Patentnummer
US06462032B1

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