4-Nitrophthalide → 4-Amino-1,3-dihydro-2-benzofuran-1-one

HRID 1467501Notes

Reaction equation

HRID 1467501 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[CH2:6][O:7][C:8]2=[O:13])([O-])=O>C(OCC)(=O)C.[Pd]>[NH2:1][C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[CH2:6][O:7][C:8]2=[O:13]

Participants

4

Reactant 1

HCID 12116924-Nitrophthalide

Product 1

HCID 122846494-Amino-1,3-dihydro-2-benzofuran-1-oneYield 96.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
25 °C

Procedure

A suspension of 4-nitroisobenzofuran-1(3H)-one (1.0 g, 5.58 mmol) and 10% Pd/C (0.1 g) in ethyl acetate (30 mL) was purged in 1 atm hydrogen and stirred at 25° C. for 3 hr. The mixture was filtered, and the filtrate was concentrated to give 4-aminoisobenzofuran-1(3H)-one (0.8 g, yield 96%) as a off-white solid. MS (ESI) m/z: 150 (M+1)+. 1H-NMR (400 MHz, CDCl3) δ 3.82 (s, br 1H), 5.19 (s, 3H), 6.91-6.95 (m, 1H), 7.32-7.36 (m, 2H).

Workup

  1. customwas purged in 1 atm hydrogen
  2. filtrationThe mixture was filtered
  3. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-609bfc58435f498ab5e89268de70ada3
Source dataset
uspto-grants-2015_04
Patent number
US08999987B2

Reaction notes

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