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

HRID 2249941Notes

Reaction equation

HRID 2249941 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-438a2df07585439682976b9c6cbf888e
Source dataset
uspto-grants-2008_01
Patent number
US07314872B2

Reaction notes

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