2,4-Dimethoxybenzaldehyde → 5-{[(2,4-Dimethoxyphenyl)methyl]amino}-2-benzofuran-1(3H)-one

HRID 1829025Notes

Reaction equation

HRID 1829025 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:7](=[O:8])[O:6][CH2:5]2.[CH3:12][O:13][C:14]1[CH:21]=[C:20]([O:22][CH3:23])[CH:19]=[CH:18][C:15]=1[CH:16]=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>CC(O)=O.CN(C=O)C.CCOC(C)=O>[CH3:12][O:13][C:14]1[CH:21]=[C:20]([O:22][CH3:23])[CH:19]=[CH:18][C:15]=1[CH2:16][NH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:7](=[O:8])[O:6][CH2:5]2

Participants

6

Reactant 3

HCID 691752,4-DimethoxybenzaldehydeHCID 7206695-AminophthalideHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 220615235-{[(2,4-Dimethoxyphenyl)methyl]amino}-2-benzofuran-1(3H)-oneYield 82%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 21926011acetic acid N,N-dimethylformamideSolvent

Procedure

To a stirred solution of 5-aminophthalide (11.7 g, 78 mmol) and 2,4-dimethoxybenzaldehyde (15.5 g, 93.6 mmol) in 1% AcOH/DMF (60 ml), was added sodium triacetoxyborohydride (50.0 g, 236 mmol). The mixture was stirred at room temperature for 16 hours, diluted with EtOAc (400 ml), washed with saturated NaHCO3 solution (3×400 ml) and water (400 ml), dried over anhydrous Na2SO4, and evaporated to provide a crude product. Trituration of the crude product with MEOH gave 5-(2,4-dimethoxy-benzylamino)-3H-isobenzofuran-1-one as an off-white powder (19.0 g, 82%).

Workup

  1. washwashed with saturated NaHCO3 solution (3×400 ml) and water (400 ml)
  2. dry with materialdried over anhydrous Na2SO4
  3. customevaporated
  4. customto provide a crude product

Sources & evidence

ORD record
ord-27fc80294c8f45dcb84fe3afefd21b46
Source dataset
uspto-grants-2006_06
Patent number
US07060844B2

Reaction notes

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