Hydrochloric Acid → HCID 21460700, compound

HRID 2082521Notes

Reaction equation

HRID 2082521 reaction equation
[F:1][C:2]1[CH:27]=[CH:26][C:5]([C:6](=[O:25])[CH2:7][NH:8][C:9]2[C:17]3[C:12](=[CH:13][C:14]([Cl:19])=[CH:15][C:16]=3[Cl:18])[NH:11][C:10]=2[C:20]([O:22]CC)=[O:21])=[CH:4][CH:3]=1.[OH-].[Li+].O1CCCC1.Cl>O.C(OCC)(=O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:6](=[O:25])[CH2:7][NH:8][C:9]2[C:17]3[C:12](=[CH:13][C:14]([Cl:19])=[CH:15][C:16]=3[Cl:18])[NH:11][C:10]=2[C:20]([OH:22])=[O:21])=[CH:26][CH:27]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 21460677HCID 21460677, compound

Product 1

HCID 21460700HCID 21460700, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

Mix 3-[(p-fluorophenacyl)amino)-2-carbethoxy-4,6-dichloroindole (600 mg, 1.52 mmol) , lithium hydroxide (191 mg, 4.55 mmol), tetrahydrofuran (20 mL) and water (20 mL). Stir overnight at room temperature. Dilute with water (20 mL) and ethyl acetate (40 mL). Acidify with 1N HCl while stirring and separate the layers. Dry the organic phase over magnesium sulfate, filter and concentrate in vacuo. Recrystallize the residue (ethyl acetate/hexane) to yield the title compound as a white powder (440 mg, 79%); mp 259°-261° C.

Workup

  1. customseparate the layers
  2. dry with materialDry the organic phase over magnesium sulfate
  3. filtrationfilter
  4. concentrationconcentrate in vacuo
  5. customRecrystallize the residue (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-bc4bff5fc47e480c8be5328b8edc31ff
Source dataset
uspto-grants-1993_02
Patent number
US05189054

Reaction notes

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