5-Fluoro-1-(4-methoxybenzyl)indoline-2,3-dione → 5-Fluoro-1-(4-methoxy-benzyl)-1,3-dihydro-indol-2-one

HRID 15267Notes

Reaction equation

HRID 15267 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=1)[C:6](=[O:20])[C:5]2=O>O.NN.C(O)C.O>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=1)[C:6](=[O:20])[CH2:5]2

Participants

5

Reactant 1

HCID 76771005-Fluoro-1-(4-methoxybenzyl)indoline-2,3-dione

Product 1

HCID 210822565-Fluoro-1-(4-methoxy-benzyl)-1,3-dihydro-indol-2-oneYield 90.3%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 24654Hydrazine hydrate (1:1)Solvent

Procedure

A solution of 5-fluoro-1-(4-methoxy-benzyl)-1H-indole-2,3-dione (7.1 g, 24.9 mmol) in hydrazine hydrate (35 mL) and ethanol (15 mL) was refluxed overnight, diluted with water and extracted twice with ethyl acetate. The combined organics were dried over Na2SO4, filtered and concentrated. The residue was purified by silica gel chromatography using a gradient of 0-100% ethyl acetate in hexane to afford 6.1 g (90%) of 5-fluoro-1-(4-methoxy-benzyl)-1,3-dihydro-indol-2-one; 1H NMR (CDCl3, 400 MHz) δ 3.59 (s, 2H), 3.77 (s, 3H), 4.83 (s, 2H), 6.63 (dd, 1H, J1=4.2, J2=8.6), 6.82-6.91 (m, 3H), 6.96-7.01 (m, 1H), 7.19-7.23 (m, 1H), 7.27-7.31 (m, 1H); HPLC-MS calcd. for C16H14FNO2 (M+H+) 272.1, found 272.3.

Workup

  1. extractionextracted twice with ethyl acetate
  2. dry with materialThe combined organics were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-148284c2df294b9cbe8e60a1deeeaee8
Source dataset
uspto-grants-2010_06
Patent number
US07732449B2

Reaction notes

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