ChemicalBook CAS DataBase List Indolo[3,2,1-de]acridin-8-one

Indolo[3,2,1-de]acridin-8-one synthesis

11synthesis methods

Product Name:Indolo[3,2,1-de]acridin-8-one
CAS Number:32081-26-8
Molecular formula:C19H11NO
Molecular Weight:269.3

66131-59-7
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32081-26-8
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Yield:32081-26-8 60%

Reaction Conditions:

with polyphosphoric acid at 180; for 4 h;

Steps:

2.2.2 8H-indolo[3,2,1-de]acridin-8-one (3)

In a one-neck flask, carbazole (3.3g, 19.9mmol), methyl 2-iodobenzoate (5.7g, 21.8mmol), Cu (0.5g, 7.1mmol), CuI (0.34g, 1.8mmol) and K₂CO₃ (4.2g, 30.4mmol) were dissolved in 30mL 1,2-dichlorobenzene, then heated the mixture to reflux for 12h under nitrogen. After the reaction was completed fully, the mixture was allowed to cool to room temperature and then CH₂Cl₂ (50mL) was poured into the mixture. Filtered the mixture and washed the cake with CH₂Cl₂, concentrated the filtrate by a rotary evaporator, then recrystallization the product from the concentrated solution by ethanol to obtain a pale yellow solid 5.4g, 89%. ¹H NMR (400MHz, CDCl₃, TMS) δ: 8.12 (t, J=8.0Hz, 3H), 7.75 (t, J=7.6Hz, 1H), 7.59 (t, J=7.6Hz, 2H), 7.37 (t, J=7.6Hz, 2H), 7.26 (t, J=6.0Hz, 2H), 7.12 (d, J=8.2Hz, 2H), 3.18 (s, 3H). Moreover, in a one-neck flask, put the previous product methyl 2-(9H-carbazol-9-yl)benzoate (2.0g, 6.6mmol) into polyphosphoric acid (10mL), heated the mixture to 180°C for 4h. Cooled the mixture to about 80°C after the reaction had full completed, poured H₂O (15mL) into the mixture and extracted with CH₂Cl₂ (20mL×3). The organic layer was dried over anhydrous MgSO₄ and concentrated this using a rotary evaporator. The crude materials were purified by silica gel column chromatography (petroleum ether/CH₂Cl₂=3: 1 v/v) to obtain a pale yellow solid 1.2g, 60%. ¹H NMR (400MHz, CDCl₃, TMS) δ: 8.68 (dd, J=8.0, 1.6Hz, 1H), 8.45 (dd, J=7.6, 1.2Hz, 2H), 8.36 (dd, J=7.6, 1.2Hz, 1H), 8.30 (d, J=8.4Hz, 1H), 8.20-8.17 (m, 1H), 7.90-7.84 (m, 1H), 7.67-7.60 (m, 2H), 7.50-7.44 (m, 2H). ¹³C NMR (126MHz, CDCl₃) δ: 134.10, 129.18, 127.92, 125.24, 124.52, 123.46, 123.21, 123.12, 121.64, 115.66, 114.11. HRMS (m/z): [M+H]^- calcd for C₁₉H₁₁NO, 270.0919; found, 270.0915.