Stannous chloride dihydrate → 6-Aminophthalide

HRID 1665783Notes

Reaction equation

HRID 1665783 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.O.O.Cl[Sn]Cl>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

4

Reactant 2

HCID 61436Stannous chloride dihydrateHCID 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 g, 0.080 mol) in HCl/H2O (375 mL/125 mL) was added SnCl2.2H2O (75 g, 0.33 mol). The reaction mixture was heated at reflux for 4 h before it was quenched with water and extracted with EtOAc (300 mL×3). The organics were dried over Na2SO4 and evaporated in vacuo to give 6-aminoisobenzofuran-1(3H)-one (10 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 before it
  3. customwas quenched with water
  4. extractionextracted with EtOAc (300 mL×3)
  5. dry with materialThe organics were dried over Na2SO4
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-ea53392b370f4b1caa949ba1a836e107
Source dataset
uspto-grants-2011_10
Patent number
US08039491B2

Reaction notes

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