Ammonium Chloride → 3-(3-amino-4-methoxybenzylidene)-3H-isobenzofuran-1-one

HRID 459779Notes

Reaction equation

HRID 459779 reaction equation
[CH3:1][O:2][C:3]1[CH:19]=[CH:18][C:6]([CH:7]=[C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10](=[O:17])[O:9]2)=[CH:5][C:4]=1[N+:20]([O-])=O.[Cl-].[NH4+]>[Fe].O>[NH2:20][C:4]1[CH:5]=[C:6]([CH:18]=[CH:19][C:3]=1[O:2][CH3:1])[CH:7]=[C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10](=[O:17])[O:9]1

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 686246993-(4-methoxy-3-nitrobenzylidene)-3H-isobenzofuran-1-one

Product 1

HCID 686248893-(3-amino-4-methoxybenzylidene)-3H-isobenzofuran-1-oneYield 65.6%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

A stirred mixture of the above crude 3-(4-methoxy-3-nitrobenzylidene)-3H-isobenzofuran-1-one (2.5 g, 0.0085 mol), industrial methylated spirit (40 ml), water (30 ml) and ammonium chloride (0.91 g, 0.017 mol) was heated to 70° C., and iron powder (4.76 g, 0.085 gatom) was added in portions. When the addition was complete, the stirred mixture was heated under reflux for a further 2 hours, then it was filtered while hot through Celite. The collected inorganic solids were washed with hot industrial methylated spirit (3×80 ml), then the filtrate and washings were combined and the solvent was removed in vacuo. The residue was triturated with water (50 ml) and the resulting solid was collected by filtration and dissolved in ethyl acetate (300 ml). The solution was filtered, the filtrate was concentrated in vacuo and the residue was triturated with industrial methylated spirit (10 ml). The resulting solid was collected by filtration and dried in vacuo for 24 hours to give 3-(3-amino-4-methoxybenzylidene)-3H-isobenzofuran-1-one (1.49 g) as a yellow solid, m.pt. 148–153° C.; m/z (M+H)+. 268, 100% purity.

Workup

  1. additionWhen the addition
  2. temperaturethe stirred mixture was heated
  3. temperatureunder reflux for a further 2 hours
  4. filtrationit was filtered while hot through Celite
  5. washThe collected inorganic solids were washed with hot industrial methylated spirit (3×80 ml)
  6. customthe solvent was removed in vacuo
  7. customThe residue was triturated with water (50 ml)
  8. filtrationthe resulting solid was collected by filtration
  9. dissolutiondissolved in ethyl acetate (300 ml)
  10. filtrationThe solution was filtered
  11. concentrationthe filtrate was concentrated in vacuo
  12. customthe residue was triturated with industrial methylated spirit (10 ml)
  13. filtrationThe resulting solid was collected by filtration
  14. customdried in vacuo for 24 hours

Sources & evidence

ORD record
ord-0419308258f84f33aab2a1ca61857766
Source dataset
uspto-grants-2007_03
Patent number
US07196085B2

Reaction notes

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