6-Chloro-4-nitroisobenzofuran-1(3H)-one → 4-Amino-6-chloroisobenzofuran-1(3H)-one

HRID 907971Notes

Reaction equation

HRID 907971 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][O:7][C:8]2=[O:11])=[C:4]([N+:12]([O-])=O)[CH:3]=1.[H][H]>CCOC(C)=O.[Pd]>[NH2:12][C:4]1[CH:3]=[C:2]([Cl:1])[CH:10]=[C:9]2[C:5]=1[CH2:6][O:7][C:8]2=[O:11]

Participants

5

Reactant 2

HCID 672581206-Chloro-4-nitroisobenzofuran-1(3H)-oneHCID 178418361HCID 178418361, compound

Product 1

HCID 672613234-Amino-6-chloroisobenzofuran-1(3H)-oneYield 90%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A suspension of 6-chloro-4-nitroisobenzofuran-1(3H)-one (5 g, 23.5 mmol) and Pd/C (10%, 500 mg) in EtOAc (250 mL) was stirred at 25° C. under 1 atm of hydrogen for 12 hr. The mixture was filtered, and the cake was washed with EtOAc (100 mL×3). The filtrate was concentrated to give the title compound (3.87 g, yield 90%) as a white solid. LC-MS (ESI) m/z: 184 (M+1)+.

Workup

  1. filtrationThe mixture was filtered
  2. washthe cake was washed with EtOAc (100 mL×3)
  3. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-8ec3741d60594efcbfd0e32427da1b9c
Source dataset
uspto-grants-2011_09
Patent number
US08012976B2

Reaction notes

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