Water → HCID 57136892, compound

HRID 2082529Notes

Reaction equation

HRID 2082529 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:26]=[CH:27][CH:28]=1)[C:5](=[O:25])[CH2:6][CH2:7][NH:8][C:9]1[C:17]2[C:12](=[CH:13][C:14]([Cl:19])=[CH:15][C:16]=2[Cl:18])[NH:11][C:10]=1[C:20]([O:22]CC)=[O:21].[OH-].[Li+].O1CCCC1.O>C(OCC)(=O)C>[F:1][C:2]1[CH:3]=[C:4]([CH:26]=[CH:27][CH:28]=1)[C:5](=[O:25])[CH2:6][CH2:7][NH:8][C:9]1[C:17]2[C:12](=[CH:13][C:14]([Cl:19])=[CH:15][C:16]=2[Cl:18])[NH:11][C:10]=1[C:20]([OH:22])=[O:21]

Participants

6

Reactant 4

HCID 962WaterHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 57311472HCID 57311472, compound

Product 1

HCID 57136892HCID 57136892, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Mix 3-[(m-fluorophenacyl)methylamino]-2-carbethoxy-4,6-dichloroindole (700 mg, 1.7 mmol), lithium hydroxide (210 mg, 5 mmol), tetrahydrofuran (10 mL) and water (10 mL). Stir for 24 hours at room temperature. Dilute with ethyl acetate (40 mL). Acidify 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 (590 mg, 91%); mp 270°-280° C.

Workup

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

Sources & evidence

ORD record
ord-7e54a735b0f847c1bf16a3647b571216
Source dataset
uspto-grants-1993_02
Patent number
US05189054

Reaction notes

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