Lithium Hydroxide → HCID 56983920, compound

HRID 2396361Notes

Reaction equation

HRID 2396361 reaction equation
[F:1][C:2]1[CH:28]=[CH:27][C:5]([C:6](=[O:26])[CH2:7][CH2:8][NH:9][C:10]2[C:18]3[C:13](=[CH:14][C:15]([Cl:20])=[CH:16][C:17]=3[Cl:19])[NH:12][C:11]=2[C:21]([O:23]CC)=[O:22])=[CH:4][CH:3]=1.[OH-].[Li+].C(OCC)(=O)C>O1CCCC1.O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:6](=[O:26])[CH2:7][CH2:8][NH:9][C:10]2[C:18]3[C:13](=[CH:14][C:15]([Cl:20])=[CH:16][C:17]=3[Cl:19])[NH:12][C:11]=2[C:21]([OH:23])=[O:22])=[CH:27][CH:28]=1

Participants

6

Reactant 3

HCID 3939Lithium HydroxideHCID 8857Ethyl AcetateHCID 57123645HCID 57123645, compound

Product 1

HCID 56983920HCID 56983920, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

Dissolve 3-[(p-fluorophenacyl)methylamino]-2-carbethoxy-4,6-dichloroindole (660 mg, 1.61 mmol) in tetrahydrofuran (5 mL) and water (5 mL). Add lithium hydroxide (203 mg, 4.8 mmol) and stir for 24 hours at room temperature. Dilute the reaction with water (20 mL) and ethyl acetate (50 mL) and acidify. Separate the layers and dry the organic phase over magnesium sulfate, filter and dilute the filtrate with hexane (100 mL). Recrystallize from this solution to yield the title compound as a white powder (550 mg, 90%).

Workup

  1. additionDilute
  2. customSeparate the layers
  3. dry with materialdry the organic phase over magnesium sulfate
  4. filtrationfilter
  5. additiondilute the filtrate with hexane (100 mL)
  6. customRecrystallize from this solution

Sources & evidence

ORD record
ord-b44ce83a5fa14fdc82f88e17f089747e
Source dataset
uspto-grants-1996_02
Patent number
US05491153

Reaction notes

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