Benzyl Chloride → 3-Benzyloxy-6-chloro-5,9-diaza-benzo[c]fluoren-7-one

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Reaktionsgleichung

[Cl:1][C:2]1[C:14]2[C:13](=[O:15])[C:12]3[CH:11]=[N:10][CH:9]=[CH:8][C:7]=3[C:6]=2[C:5]2[CH:16]=[CH:17][C:18]([OH:20])=[CH:19][C:4]=2[N:3]=1.[CH2:21](Cl)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.ClCCl>[CH2:21]([O:20][C:18]1[CH:17]=[CH:16][C:5]2[C:6]3[C:7]4[CH:8]=[CH:9][N:10]=[CH:11][C:12]=4[C:13](=[O:15])[C:14]=3[C:2]([Cl:1])=[N:3][C:4]=2[CH:19]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Komponenten

Reaktionsbedingungen

Temperatur: 90 °C

Versuchsvorschrift

6-Chloro-3-hydroxy-5,9-diaza-benzo[c]fluoren-7-one (Example 34a) (27 mg) was dissolved in DMF (2 ml). To the solution were added benzyl chloride (0.016 ml) and potassium carbonate (29 mg). The mixture was stirred at 90° C. for 2 hours. The reaction mixture was dissolved in dichloromethane and the mixture was washed with water. The organic layer was dried over anhydrous sodium sulfate and evaporated to dryness. The residue was purified by silica gel column chromatography developed by dichloromethane and dichloromethane-MeOH=50:1. The desired product (12 mg) was obtained as a light yellow solid. EI−MS: m/z 372 (M+); 1H-NMR (CDCl3): δ5.25 (2H, s), 7.30-7.55 (7H, m), 8.00 (1H, dd, J=5 Hz, 1 Hz), 8.36 (1H, d, J=9Hz), 8.95 (1H, d, 5 Hz), 9.03 (1H, d, J=1 Hz).

Aufarbeitung

washthe mixture was washed with water
dry with materialThe organic layer was dried over anhydrous sodium sulfate
customevaporated to dryness
customThe residue was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag: ord-e47788040ab948c296139d9c99a7fbad
Quelldatensatz: uspto-grants-2004_01
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US06680326B2

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