Acetic Acid → 5-{[(2,4-Dimethoxyphenyl)methyl]amino}-1,3-dihydro-2H-indol-2-one

HRID 1829081Notes

Reaction equation

HRID 1829081 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[CH2:5]2.[CH3:12][O:13][C:14]1[CH:15]=[C:16]([CH:19]=[C:20]([O:22][CH3:23])[CH:21]=1)C=O.[C:24](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].CC(O)=O>CN(C=O)C>[CH3:23][O:22][C:20]1[CH:21]=[C:14]([O:13][CH3:12])[CH:15]=[CH:16][C:19]=1[CH2:24][NH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[CH2:5]2

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 817473,5-DimethoxybenzaldehydeHCID 27732135-Amino-2-oxindoleHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 220615095-{[(2,4-Dimethoxyphenyl)methyl]amino}-1,3-dihydro-2H-indol-2-oneYield 51%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 5-aminooxindole (1.0 g, 6.75 mmol), 3,5-dimethoxybenzaldehyde (1.35 g, 8.12 mmol), sodium triacetoxyborohydride (4.3 g, 20.3 mmol), and AcOH (0.5 ml) in DMF (15 ml) was stirred at room temperature for 3.5 hours. The mixture was partitioned between saturated NaHCO3 solution (50 ml) and CHCl3 (50 ml). The aqueous layer was extracted again with CHCl3 (2×50 ml). The organic layers were combined, washed with saturated NaHCO3 solution (50 ml), water (2×75 ml), dried over Na2SO4, and poured into Et2O (100 ml) with stirring. The resulting solid was filtered, washed with Et2O and dried to give 5-(2,4-dimethoxy-benzylamino)-1,3-dihydro-indol-2-one as a brown solid (1.02 g, 51%).

Workup

  1. customThe mixture was partitioned between saturated NaHCO3 solution (50 ml) and CHCl3 (50 ml)
  2. extractionThe aqueous layer was extracted again with CHCl3 (2×50 ml)
  3. washwashed with saturated NaHCO3 solution (50 ml), water (2×75 ml)
  4. dry with materialdried over Na2SO4
  5. additionpoured into Et2O (100 ml)
  6. stirringwith stirring
  7. filtrationThe resulting solid was filtered
  8. washwashed with Et2O
  9. customdried

Sources & evidence

ORD record
ord-d5a68e7aefae44db829dd3b38d4b9272
Source dataset
uspto-grants-2006_06
Patent number
US07060844B2

Reaction notes

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