6-Fluoro-4-nitro-2-benzofuran-1(3H)-one → 4-Amino-6-fluoroisobenzofuran-1(3H)-one

HRID 1467577Notes

Reaction equation

HRID 1467577 reaction equation
[F: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]([F:1])[CH:10]=[C:9]2[C:5]=1[CH2:6][O:7][C:8]2=[O:11]

Participants

5

Reactant 2

HCID 575191766-Fluoro-4-nitro-2-benzofuran-1(3H)-oneHCID 178418361HCID 178418361, compound

Product 1

HCID 672589744-Amino-6-fluoroisobenzofuran-1(3H)-oneYield 92.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A suspension of 6-fluoro-4-nitroisobenzofuran-1(3H)-one (9.6 g, 48.7 mmol) and Pd/C (10%, 1 g) in EtOAc (300 mL) was stirred at 25° C. under 1 atmosphere of hydrogen for 12 hr. TLC (petroleum ether/EtOAc=2:1) showed the reaction was complete. The mixture was filtered, and the cake was washed with EtOAc (100 mL×3). The filtrate was concentrated to give 4-amino-6-fluoroisobenzofuran-1(3H)-one (7.5 g, yield 92%) as a white solid. 1H-NMR (400 MHz, CDCl3) δ (ppm): 3.85 (br s, 2H), 5.14-5.15 (d, 2H), 6.62-6.65 (dd, 1H), 6.98-7.00 (dd, 1H); LC-MS (ESI) m/z: 168 (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-dd81aa56a37a459a83e3e6b6bf139681
Source dataset
uspto-grants-2015_04
Patent number
US08999987B2

Reaction notes

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