2,4-Dimethoxybenzaldehyde → 3-[6-(2,4-Dimethoxy-benzylamino)-3H-isobenzofuran-1-ylidene]-1,3-dihydro-indol-2-one

HRID 1829016Notes

Reaction equation

HRID 1829016 reaction equation
[NH2:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][O:7][C:8]2=[C:11]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[NH:13][C:12]2=[O:20])=[CH:4][CH:3]=1.[CH3:21][O:22][C:23]1[CH:30]=[C:29]([O:31][CH3:32])[CH:28]=[CH:27][C:24]=1[CH:25]=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>CC(O)=O.CN(C=O)C.C(Cl)(Cl)Cl>[CH3:21][O:22][C:23]1[CH:30]=[C:29]([O:31][CH3:32])[CH:28]=[CH:27][C:24]=1[CH2:25][NH:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][O:7][C:8]2=[C:11]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[NH:13][C:12]2=[O:20])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 691752,4-DimethoxybenzaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 696591993-(6-Amino-2-benzofuran-1(3H)-ylidene)-1,3-dihydro-2H-indol-2-one

Product 1

HCID 696593393-[6-(2,4-Dimethoxy-benzylamino)-3H-isobenzofuran-1-ylidene]-1,3-dihydro-indol-2-one

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 21926011acetic acid N,N-dimethylformamideSolvent

Procedure

To a stirred solution of 3-(6-amino-3H-isobenzofuran-1-ylidene)-1,3-dihydro-indol-2-one (1 g, 3.79 mmol) and 2,4-dimethoxybenzaldehyde (0.75 g, 4.54 mmol) in 1% AcOH/DMF (30 ml), was added sodium triacetoxyborohydride (3.2 g, 15.1 mmol). The mixture was stirred at room temperature for 16 hours, diluted with CHCl3 (200 ml), washed with saturated aqueous NaHCO3 solution (200 ml) and water (2×200 ml), dried over anhydrous Na2SO4. Removal of the solvent provided the crude product. Recrystallization of the crude product from MeOH resulted in 3-[6-(2,4-dimethoxy-benzylamino)-3H-isobenzofuran-1-ylidene]-1,3-dihydro-indol-2-one as a bright yellow solid (1.3 g, 83%).

Workup

  1. washwashed with saturated aqueous NaHCO3 solution (200 ml) and water (2×200 ml)
  2. dry with materialdried over anhydrous Na2SO4
  3. customRemoval of the solvent
  4. customprovided the crude product
  5. customRecrystallization of the crude product from MeOH
  6. customresulted in 3-[6-(2,4-dimethoxy-benzylamino)-3H-isobenzofuran-1-ylidene]-1,3-dihydro-indol-2-one as a bright yellow solid (1.3 g, 83%)

Sources & evidence

ORD record
ord-08146554d16840abbfc2423f59af9b7f
Source dataset
uspto-grants-2006_06
Patent number
US07060844B2

Reaction notes

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