Acetaldehyde → 3-(6-Ethylamino-3H-isobenzofuran-1-ylidene)-1,3-dihydro-indol-2-one

HRID 1829012Notes

Reaction equation

HRID 1829012 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.[CH:21](=O)[CH3:22].[C:24](O[BH-](OC(=O)C)OC(=O)C)(=O)[CH3:25].[Na+]>>[CH2:21]([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)[CH3:22].[CH2:24]([N:1]([CH2:21][CH3:22])[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)[CH3:25]

Participants

5

Reactant 3

HCID 177AcetaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 696591993-(6-Amino-2-benzofuran-1(3H)-ylidene)-1,3-dihydro-2H-indol-2-one

Product 2

HCID 696597463-(6-Diethylamino-3H-isobenzofuran-1-ylidene)-1,3-dihydro-indol-2-oneYield 5%HCID 696600583-(6-Ethylamino-3H-isobenzofuran-1-ylidene)-1,3-dihydro-indol-2-oneYield 61%

Procedure

A mixture of 3-(6-Amino-3H-isobenzofuran-1-ylidene)-1,3-dihydro-indol-2-one (581 mg, 2.20 mmol), acetaldehyde (116 mg, 2.64 mmol), and sodium triacetoxyborohydride (606 mg, 2.86 mmol) was stirred at room temperature for 3 h. The reaction was then partitioned between ethyl acetate and H2O. The organic phase was washed with dilute aqueous NaHCO3 solution, H2O, brine and then dried with Na2SO4. The solvent was removed in vacuo and the residue was dissolved in CHCl3/MeOH and purified by chromatography (silica gel, hexanes/EtOAc, 7:3) to give 3-(6-Ethylamino-3H-isobenzofuran-1-ylidene)-1,3-dihydro-indol-2-one (395.1 mg, 61%) as a yellow solid and 3-(6-Diethylamino-3H-isobenzofuran-1-ylidene)-1,3-dihydro-indol-2-one (32.9 mg, 5%) as a yellow solid.

Workup

  1. customThe reaction was then partitioned between ethyl acetate and H2O
  2. washThe organic phase was washed with dilute aqueous NaHCO3 solution, H2O, brine
  3. dry with materialdried with Na2SO4
  4. customThe solvent was removed in vacuo
  5. dissolutionthe residue was dissolved in CHCl3/MeOH
  6. custompurified by chromatography (silica gel, hexanes/EtOAc, 7:3)

Sources & evidence

ORD record
ord-3eb2e5fe302f4a7291cbdd9fc5702c3c
Source dataset
uspto-grants-2006_06
Patent number
US07060844B2

Reaction notes

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