Triethylamine → Ethyl-1-(4-methoxynaphthylsulfonyl)-2,3-dihydroindole-3-acetate

HRID 1174527Notes

Reaction equation

HRID 1174527 reaction equation
[CH3:1][O:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([S:13](Cl)(=[O:15])=[O:14])=[CH:5][CH:4]=1.[CH2:17]([O:19][C:20](=[O:31])[CH2:21][CH:22]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[NH:24][CH2:23]1)[CH3:18].C(N(CC)CC)C>ClCCl.O>[CH2:17]([O:19][C:20](=[O:31])[CH2:21][CH:22]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[N:24]([S:13]([C:6]2[C:7]3[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=3)[C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)(=[O:15])=[O:14])[CH2:23]1)[CH3:18]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 167755014-Methoxynaphthalene-1-sulfonyl chlorideHCID 21795444Ethyl (2,3-dihydro-1H-indol-3-yl)acetate

Product 1

HCID 68773619Ethyl-1-(4-methoxynaphthylsulfonyl)-2,3-dihydroindole-3-acetateYield 94%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

4-Methoxynaphthylsulfonyl chloride (1.25 g, 5 mmol.) was added portionwise to ethyl-2,3-dihydro-1H indole-3-acetate (1 g, 5 mmol) in dichloromethane (20 cm3), containing triethylamine (1 cm3, 7 mmol) at 0° C. After stirring at room temperature for 4 h, the reaction was diluted with water and the organic layer was separated, dried and concentrated to give ethyl-1-(4-methoxynaphthylsulfonyl)-2,3-dihydroindole-3-acetate as an oil (2 g, 4.7 mmol, 94%). This was then taken up in ethyl alcohol (20 cm3) and aqueous sodium hydroxide (4N, 7 cm3, 28 mmol) was added and the resulting mixture was stirred and heated together at reflux for 2 h. The reaction mixture was then cooled and the ethyl alcohol was removed under reduced pressure. The residue was taken up in water and extracted once with diethyl ether to remove any unreacted ester. The aqueous mixture was then acidified and the product extracted into ethyl acetate. The organic layer was separated, dried and concentrated to provide 1-(4-methoxynaphthylsulfonyl)-2,3-dihydro-indole-3-acetic acid as a solid (1.17 g, 3.00 mmol, 64%).

Workup

  1. customthe organic layer was separated
  2. customdried
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-07e7d90f43c7492f9c820b04ff0bd081
Source dataset
uspto-grants-2010_11
Patent number
US07838518B2

Reaction notes

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