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

HRID 1476922Notes

Reaction equation

HRID 1476922 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

5

Reactant 3

HCID 6344DichloromethaneHCID 86582-MethoxybenzaldehydeHCID 118312-Nitrofluorene

Product 1

HCID 712714629-[(2-Methoxyphenyl)methylidene]-2-nitro-9H-fluorene

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

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)

Workup

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

Sources & evidence

ORD record
ord-957f97fa737e4afdaa1204b9fa1f63a3
Source dataset
uspto-grants-2016_08
Patent number
US09402850B2

Reaction notes

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