Hydrochloric Acid → 6-Amino-1,3-dihydro-2H-indol-2-one

HRID 1887690Notes

Reaction equation

HRID 1887690 reaction equation
CO.Cl.[N+:4]([C:7]1[CH:12]=[C:11]([N+:13]([O-])=O)[CH:10]=[CH:9][C:8]=1[CH2:16][C:17]([OH:19])=O)([O-])=O.[H][H]>CCO.[Pd]>[NH2:13][C:11]1[CH:12]=[C:7]2[C:8]([CH2:16][C:17](=[O:19])[NH:4]2)=[CH:9][CH:10]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 2215132,4-Dinitrophenylacetic acidHCID 178418361HCID 178418361, compound

Product 1

HCID 5905386-Amino-1,3-dihydro-2H-indol-2-one

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

Methanol (15 mL) and 1.25 M HCl in EtOH (10 ml) was added to 2,4-dinitrophenylacetic acid (837 mg, 3.7 mmol) and Pd/C (10%; 205 mg) under Argon. The argon balloon was replaced with a hydrogen balloon and it was stirred at RT for 12 h and at 50° C. for 24 h. It was cooled to RT and filtered through celite. The solvent was removed and the residue was purified by silica gel chromatography (DCM/methanol gradient) to give the title compound as a red solid.

Workup

  1. temperatureIt was cooled to RT
  2. filtrationfiltered through celite
  3. customThe solvent was removed
  4. customthe residue was purified by silica gel chromatography (DCM/methanol gradient)

Sources & evidence

ORD record
ord-a78c1beab9024f5abc6b96b3b8bf59f3
Source dataset
uspto-grants-2013_08
Patent number
US08501763B2

Reaction notes

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