Dichloromethane → 3-((2-Nitro-9H-fluoren-9-ylidene)methyl)pyridin-2(1H)-one

HRID 578077Notes

Reaction equation

HRID 578077 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].[O:17]=[C:18]1[C:23]([CH:24]=O)=[CH:22][CH:21]=[CH:20][NH:19]1.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:24][C:23]3[C:18](=[O:17])[NH:19][CH:20]=[CH:21][CH:22]=3)[C:6]=2[CH:5]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 118312-NitrofluoreneHCID 70621962-Oxo-1,2-dihydropyridine-3-carbaldehyde

Product 1

HCID 712719243-((2-Nitro-9H-fluoren-9-ylidene)methyl)pyridin-2(1H)-one

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
85 °C

Procedure

To a solution of 2-nitrofluorene (326 mg, 1.54 mmol) and 2-oxo-1,2-dihydro-pyridine-3-carbaldehyde (19 mg, 1.54 mmol) in 10 mL of methanol was added KF—Al2O3 (224 mg, 1.38 mmol). The resulting mixture was stirred at 85° C. After 24 hrs, TLC indicated that a new product was produced and lots of starting material was still remained. 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 60% EtOAc in hexane afforded 26 mg of CYD-1-93 as a yellow solid. 1H-NMR (600 MHz, d6-DMSO) δ 12.18 (br s, 2H), 8.77 (d, 1H, J=1.8 Hz), 8.52 (d, 1H, J=1.8 Hz), 8.28 (m, 2H), 8.15 (m, 2H), 8.10 (d, 1H, J=7.8 Hz), 8.06 (m, 2H), 7.97 (m, 2H), 7.86 (m, 2H), 7.80 (s, 1H), 7.63 (m, 1H), 7.59 (m, 1H), 7.49 (m, 3H), 7.37 (m, 1H), 6.40 (m, 2H). 13C-NMR (150 MHz, CDCl3) δ 161.2, 161.1, 146.9, 146.2, 146.1, 143.6, 142.1, 141.7, 140.5, 139.6, 138.3, 137.3, 136.1, 136.0, 133.6, 133.4, 129.3, 129.1, 129.0, 128.8, 127.9, 127.4, 126.1, 125.9, 124.0, 123.9, 123.5, 121.9, 121.5, 121.1, 120.7, 120.5, 119.0, 105.1, 105.0.

Workup

  1. customwas produced
  2. filtrationThe insoluble solid was filtrated
  3. concentrationthe filtrate was concentrated under vacuum
  4. customto give a yellow solid, which
  5. customwas purified by silica gel column
  6. washeluting with 60% EtOAc in hexane
  7. customafforded 26 mg of CYD-1-93 as a yellow solid

Sources & evidence

ORD record
ord-1975994eb1af488eb80c3cd487091bc4
Source dataset
uspto-grants-2015_05
Patent number
US09040567B2

Reaction notes

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