2-(2-Fluorophenyl)-5,6-methylenedioxyquinolin-4-one → 2-(2-Fluorophenyl)-5,6-dihydroxyquinolin-4-one

HRID 38633Notes

Reaction equation

HRID 38633 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH2:17][C:16](=[O:18])[C:15]2[C:10](=[CH:11][CH:12]=[C:13]3[O:21]C[O:19][C:14]3=2)[N:9]=1>CO.[Pd]>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH2:17][C:16](=[O:18])[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([OH:21])[C:14]=2[OH:19])[N:9]=1

Participants

4

Reactant 1

HCID 666590942-(2-Fluorophenyl)-5,6-methylenedioxyquinolin-4-one

Product 1

HCID 666593062-(2-Fluorophenyl)-5,6-dihydroxyquinolin-4-oneYield 13.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 19 (0.1 g, 0.35 mmol) in anhydrous MeOH (30 mL) was hydrogenated in the presence of 10% Pd/C (0.2 g) at 25±2° C. for 40 h. The catalyst was filtered off and the filtrate was evaporated. The crude was purified by column chromatography (SiO2, EtOAc: MeOH=30:1) to give 40. White solid; yield: 13.7%; mp 152-154° C.; MS (EI, 70 eV): m/z 271 (M+); IR (KBr): 1622.13 (C═O) cm−1; 1H-NMR (DMSO-d6, 200 MHz): δ 6.03 (s, 1H), 7.15 (d, J=8.8 Hz, 1H), 7.30-7.70 (m, 6H), 9.72 (s, 1H), 11.76 (s, 1H); 13C-NMR (DMSO-d6, 50 MHz): δ 107.67, 108.57, 116.75 (d, J=21.5 Hz), 120.54, 122.67, 123.36, 125.42, 126.70, 131.22, 132.49, 134.35, 144.30, 154.29, 159.43 (d, J=248.5 Hz), 176.82; Anal. calcd for C15H10FNO3: C, 66.42; H, 3.72; N, 5.16. Found: C, 66.38; H, 3.70; N, 5.15.

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe filtrate was evaporated
  3. customThe crude was purified by column chromatography (SiO2, EtOAc: MeOH=30:1)

Sources & evidence

ORD record
ord-04904fa4405840b3b91bdc91cf57ce23
Source dataset
uspto-grants-2013_09
Patent number
US08524740B2

Reaction notes

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