Phthalide → 6-Nitrophthalide

HRID 1442794Notes

Reaction equation

HRID 1442794 reaction equation
[C:1]1(=[O:10])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][O:2]1.[N+:11]([O-])([O-:13])=[O:12].[K+]>OS(O)(=O)=O>[N+:11]([C:7]1[CH:8]=[C:9]2[C:4]([CH2:3][O:2][C:1]2=[O:10])=[CH:5][CH:6]=1)([O-:13])=[O:12]

Participants

4

Reactant 2

HCID 6885PhthalideHCID 24434Potassium Nitrate

Product 1

HCID 2235846-NitrophthalideYield 81.2%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent2×

Conditions

Temperature
20 °C

Procedure

To a stirred solution of 3H-Isobenzofuran-1-one (30.0 g, 0.220 mol) in H2SO4 (38 mL) was added KNO3 (28.0 g, 0.290 mol) in H2SO4 (60 mL) at 0° C. After the addition, the mixture was stirred at 20° C. for 1 h. The reaction mixture was poured into ice and the resulting precipitate was filtered off and recrystallized from ethanol to give 6-nitroisobenzofuran-1(3H)-one (32.0 g, 80%). 1H NMR (300 MHz, CDCl3) δ 8.76 (d, J=2.1, 1H), 8.57 (dd, J=8.4, 2.1, 1H), 7.72 (d, J=8.4, 1H), 5.45 (s, 2H).

Workup

  1. additionAfter the addition
  2. additionThe reaction mixture was poured into ice
  3. filtrationthe resulting precipitate was filtered off
  4. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-572e1332670747aa9027ba0a4ccbbe20
Source dataset
uspto-grants-2010_02
Patent number
US07659268B2

Reaction notes

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