Acetic Acid → 6-Aminophthalide

HRID 2175625Notes

Reaction equation

HRID 2175625 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.C(OCC)(=O)C.C(O)(=O)C.C(=O)(O)[O-].[Na+]>O.[Fe]>[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

7

Reactant 4

HCID 176Acetic AcidHCID 8857Ethyl AcetateHCID 2235846-NitrophthalideHCID 516892Sodium Bicarbonate

Product 1

HCID 936316-Aminophthalide

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

Into a 2000 mL 3-necked round-bottom flask, was placed a solution of 6-nitroisobenzofuran-1(3H)-one (prepared as described in the previous step, 136 g, 759.78 mmol, 1.00 equiv) in water (50 mL), Fe (126.4 g), ethyl acetate (500 mL), acetic acid (180 mL). The reaction mixture was stirred for 2 h at 60° C. in an oil bath. The resulting mixture was added sodium bicarbonate 500 mL. The resulting solution was extracted with 5×500 mL of ethyl acetate. The combined organic layer was washed with 500 mL of brine, dried (Na2SO4), and concentrated under vacuum. The title compound was obtained as a yellow solid.

Workup

  1. customInto a 2000 mL 3-necked round-bottom flask, was placed
  2. extractionThe resulting solution was extracted with 5×500 mL of ethyl acetate
  3. washThe combined organic layer was washed with 500 mL of brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-53fecb95415d42338271481c87546e27
Source dataset
uspto-grants-2015_06
Patent number
US09062048B2

Reaction notes

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