Tetrahydrofuran → 4,6-Dichloro-3-[(2-oxo-2-phenylethyl)amino]-1H-indole-2-carboxylic acid

HRID 2396345Notes

Reaction equation

HRID 2396345 reaction equation
[CH2:1]([NH:10][C:11]1[C:19]2[C:14](=[CH:15][C:16]([Cl:21])=[CH:17][C:18]=2[Cl:20])[NH:13][C:12]=1[C:22]([O:24]CC)=[O:23])[C:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)=[O:3].O.[OH-].[Li+].O1CCCC1>O.C(OCC)(=O)C>[CH2:1]([NH:10][C:11]1[C:19]2[C:14](=[CH:15][C:16]([Cl:21])=[CH:17][C:18]=2[Cl:20])[NH:13][C:12]=1[C:22]([OH:24])=[O:23])[C:2]([C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1)=[O:3]

Participants

6

Reactant 3

HCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 21460706HCID 21460706, compound

Product 1

HCID 214606834,6-Dichloro-3-[(2-oxo-2-phenylethyl)amino]-1H-indole-2-carboxylic acidYield 64%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

Mix 3-[(phenacyl)amino]-2-carbethoxy-4,6-dichloroindole (300 mg, 0.79 mmol), lithium hydroxide monohydrate (2.39 mmol), tetrahydrofuran (2 mL) and water (2 mL). Stir at room temperature overnight. Dilute with water and ethyl acetate. Acidify the aqueous phase and separate the organic phase. Dry (MgSO4), evaporate the solvent in vacuo, and recrystallizethe residue (ethyl acetate/hexane) to give the title compound (175 mg, 64%).

Workup

  1. customseparate the organic phase
  2. dry with materialDry (MgSO4)
  3. customevaporate the solvent in vacuo, and recrystallizethe residue (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-861d0cc2aee148d78ad61de220dafbdf
Source dataset
uspto-grants-1996_02
Patent number
US05491153

Reaction notes

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