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

HRID 1829000Notes

Reaction equation

HRID 1829000 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(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[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]

Participants

4

Reactant 3

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

Product 1

HCID 696600583-(6-Ethylamino-3H-isobenzofuran-1-ylidene)-1,3-dihydro-indol-2-oneYield 39.1%

Procedure

A mixture of 3-(6-Amino-3H-isobenzofuran-1-ylidene)-1,3-dihydro-indol-2-one (50.0 mg, 0.189 mmol), acetaldehyde (10.0 mg, 0.227 mmol), and sodium triacetoxyborohydride (52.1 mg, 0.246 mmol) was stirred at room temperature for 2.5 h. The reaction was then partitioned between EtOAc and H2O. The organic phase was washed with H2O, brine and then dried with Na2SO4. The solvent was removed in vacuo and the residue recrystallized from EtOAc/hexanes to afford the title compound (21.6 mg, 39%) as a yellow solid.

Workup

  1. customThe reaction was then partitioned between EtOAc and H2O
  2. washThe organic phase was washed with H2O, brine
  3. dry with materialdried with Na2SO4
  4. customThe solvent was removed in vacuo
  5. customthe residue recrystallized from EtOAc/hexanes

Sources & evidence

ORD record
ord-a3fb365d86b24786bca5361cfb10800a
Source dataset
uspto-grants-2006_06
Patent number
US07060844B2

Reaction notes

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