Dichloromethane → 9-[(2-Methoxyphenyl)methylidene]-2-nitro-9H-fluorene

HRID 1476924Notes

Reaction equation

[N+:1]([C:4]1[CH:16]=[CH:15][C:14]2[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[CH2:7][C:6]=2[CH:5]=1)([O-:3])=[O:2].[CH3:17][O:18][C:19]1[CH:26]=[CH:25][CH:24]=[CH:23][C:20]=1[CH:21]=O.C(Cl)Cl>CO>[CH3:17][O:18][C:19]1[CH:26]=[CH:25][CH:24]=[CH:23][C:20]=1[CH:21]=[C:7]1[C:6]2[CH:5]=[C:4]([N+:1]([O-:3])=[O:2])[CH:16]=[CH:15][C:14]=2[C:13]2[C:8]1=[CH:9][CH:10]=[CH:11][CH:12]=2

Participants

Conditions

Temperature: 72 °C

Procedure

To a solution of 2-nitrofluorene (1.05 g, 5 mmol) and 2-methoxybenzaldehyde (0.816 g, 6 mmol) in 20 mL of methanol was added KF—Al2O3 (0.75 g, 4.5 mmol). The resulting mixture was stirred at 72° C. After 6 hrs, TLC indicated that the starting material was gone. 40 mL of CH2Cl2 was added into the reaction mixture. The insoluble solid was filtrated, and the filtrate was concentrated under vacuum to give a yellow solid, which was recrystallized from alcohol and CH2Cl2 to give 1.2 g of CYD-1-70 as a yellow solid. 1H-NMR (600 MHz, CDCl3) δ 8.84 (s, 0.36H), 8.26 (m, 1.65H), 8.10 (m, 3.05H), 8.02 (s, 0.57H), 7.55 (m, 4H), 7.24 (m, 1.24H), 7.10 (m, 0.91H), 3.84 (s, 3H). 13C-NMR (150 MHz, CDCl3) δ 157.7, 147.4, 146.6, 146.5, 144.2, 140.8, 140.0, 138.6, 137.9, 136.8, 136.6, 134.2, 134.0, 131.5, 131.2, 131.1, 130.8, 129.6, 129.5, 129.2 (2C), 128.9, 128.4, 124.5, 124.3, 124.2, 124.1, 123.9, 122.2, 121.9, 121.6, 121.1, 120.9, 120.8 (2C), 119.1, 116.6 (2C), 112.1, 112.0, 55.9 (2C).

Workup

filtrationThe insoluble solid was filtrated
concentrationthe filtrate was concentrated under vacuum
customto give a yellow solid, which
customwas recrystallized from alcohol and CH2Cl2
customto give 1.2 g of CYD-1-70 as a yellow solid

Sources & evidence

ORD record: ord-7344cd85f50a48328677620f3fc07176
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09402850B2

Reaction notes

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