Ethanol → 6-Amino-5-fluoroindolin-2-one

HRID 1655834Notes

Reaction equation

HRID 1655834 reaction equation
[F:1][C:2]1[C:3]([N+:16]([O-])=O)=[CH:4][C:5]([N+:13]([O-])=O)=[C:6]([CH2:8][C:9](OC)=[O:10])[CH:7]=1.COCCOC.C(O)C.[OH-].[Na+]>Cl.[Pd]>[NH2:16][C:3]1[CH:4]=[C:5]2[C:6]([CH2:8][C:9](=[O:10])[NH:13]2)=[CH:7][C:2]=1[F:1]

Participants

7

Reactant 4

HCID 702EthanolHCID 80711,2-DimethoxyethaneHCID 14798Sodium HydroxideHCID 11777262HCID 11777262, compound

Product 1

HCID 101035046-Amino-5-fluoroindolin-2-oneYield 84.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 313Hydrochloric AcidSolvent

Procedure

A mixture of 10% Pd on carbon (2.44 g, 10% by weight), methyl (5-fluoro-2,4-dinitrophenyl)acetate (24.4 g, 93.8 mmol), ethylene glycol dimethyl ether (100 mL) and ethanol (100 mL) is hydrogenated on a Parr hydrogenator for 11/2 hours. After the uptake of 47-48 psi, the reaction mixture is removed from the hydrogenator. The catalyst is filtered and the filtrate is concentrated in vacuo to give a dark oil. The oil is diluted with 1M hydrochloric acid, heated at reflux for 20 minutes, cooled to room temperature and the pH is adjusted to 8 with 3N sodium hydroxide solution. The pH adjusted solution is extracted with ethyl acetate and the combined organic extracts are dried and concentrated in vacuo to give the title product as a light brown solid (13.2 g, mp 185°-187° C. dec) which is identified by 1H NMR spectral analysis.

Workup

  1. custom2 hours
  2. customAfter the uptake of 47-48 psi, the reaction mixture is removed from the hydrogenator
  3. filtrationThe catalyst is filtered
  4. concentrationthe filtrate is concentrated in vacuo
  5. customto give a dark oil
  6. temperatureheated
  7. temperatureat reflux for 20 minutes
  8. extractionThe pH adjusted solution is extracted with ethyl acetate
  9. customthe combined organic extracts are dried
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9c7fefcc997449dc91eb32e8881cb4e2
Source dataset
uspto-grants-1993_10
Patent number
US05252536

Reaction notes

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