Dichloromethane → 2-[(2-Nitrofluoren-9-ylidene)methyl]phenol

HRID 1476923Notes

Reaction equation

HRID 1476923 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].[CH:17](=O)[C:18]1[C:19](=[CH:21][CH:22]=[CH:23][CH:24]=1)[OH:20].C(Cl)Cl>CO>[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)[C:7](=[CH:17][C:18]3[CH:24]=[CH:23][CH:22]=[CH:21][C:19]=3[OH:20])[C:6]=2[CH:5]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 6998SalicylaldehydeHCID 118312-Nitrofluorene

Product 1

HCID 3491562-[(2-Nitrofluoren-9-ylidene)methyl]phenol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
72 °C

Procedure

To a solution of 2-nitrofluorene (250 mg, 1.18 mmol) and salicylaldehyde (159 mg, 1.30 mmol) in 10 mL of methanol was added KF—Al2O3 (170 mg, 1.06 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 purified by silica gel column; eluting with 11% EtOAc in hexane afforded 125 mg of CYD-1-87 as a yellow solid. 1H-NMR (600 MHz, CDCl3) δ 10.05 (br s, 1H), 8.39 (s, 1H), 8.27 (dd, 1H, J=2.4 Hz, 8.4 Hz), 8.16 (d, 1H, J=8.4 Hz), 8.09 (m, 2H), 8.04 (s, 1H), 7.52 (m, 3H), 7.37 (m, 1H), 7.05 (d, 1H, J=8.4 Hz), 6.96 (t, 1H, J=7.2 Hz).

Workup

  1. filtrationThe insoluble solid was filtrated
  2. concentrationthe filtrate was concentrated under vacuum
  3. customto give a yellow solid, which
  4. customwas purified by silica gel column
  5. washeluting with 11% EtOAc in hexane
  6. customafforded 125 mg of CYD-1-87 as a yellow solid

Sources & evidence

ORD record
ord-02b7c29b5b084c33a73b0f52198d8ebc
Source dataset
uspto-grants-2016_08
Patent number
US09402850B2

Reaction notes

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