6-Nitrophthalide → 6-Aminophthalide

HRID 1442795Notes

Reaction equation

HRID 1442795 reaction equation
[N+:1]([C:4]1[CH:12]=[C:11]2[C:7]([CH2:8][O:9][C:10]2=[O:13])=[CH:6][CH:5]=1)([O-])=O>Cl.O>[NH2:1][C:4]1[CH:12]=[C:11]2[C:7]([CH2:8][O:9][C:10]2=[O:13])=[CH:6][CH:5]=1

Participants

3

Reactant 1

HCID 2235846-Nitrophthalide

Product 1

HCID 936316-AminophthalideYield 83.8%

Reagents, catalysts & solvents 1

HCID 21885828Hydrate;hydrochlorideSolvent

Procedure

To a solution of 6-nitroisobenzofuran-1(3H)-one (15.0 g, 0.0800 mol) in HCl/H2O (375 mL/125 mL) was added SnCl2-2H2O (75.0 g, 0.330 mol). The reaction mixture was heated at reflux for 4 h, quenched with water, and extracted with ethyl acetate (300 mL×3). The organic layer was dried over Na2SO4 was evaporated in vacuo to give 6-aminoisobenzofuran-1(3H)-one (10.0 g, 78%). 1H NMR (300 MHz, CDCl3) δ 7.23 (d, J=8.1, 1H), 7.13 (d, J=2.1, 1H), 6.98 (dd, J=8.1, 2.1, 1H), 5.21 (s, 2H), 3.99 (br s, 2H).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 4 h
  3. customquenched with water
  4. extractionextracted with ethyl acetate (300 mL×3)
  5. dry with materialThe organic layer was dried over Na2SO4
  6. customwas evaporated in vacuo

Sources & evidence

ORD record
ord-d24aa6f912ba4007a087a7981f37f09c
Source dataset
uspto-grants-2010_02
Patent number
US07659268B2

Reaction notes

Loading…