Hydrochloric Acid → HCID 57124046, compound

HRID 2082511Notes

Reaction equation

HRID 2082511 reaction equation
[CH2:1]([CH2:10][CH2:11][NH:12][C:13]1[C:21]2[C:16](=[CH:17][C:18]([Cl:23])=[CH:19][C:20]=2[Cl:22])[NH:15][C:14]=1[C:24]([O:26]CC)=[O:25])[C:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)=[O:3].O.O.[OH-].[Li+].Cl>O1CCCC1>[CH2:1]([CH2:10][CH2:11][NH:12][C:13]1[C:21]2[C:16](=[CH:17][C:18]([Cl:23])=[CH:19][C:20]=2[Cl:22])[NH:15][C:14]=1[C:24]([OH:26])=[O:25])[C:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)=[O:3]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 57275427HCID 57275427, compound

Product 1

HCID 57124046HCID 57124046, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Mix 3-[(phenacyl)ethylamino]-2-carbethoxy-4,6-dichloroindole (600 mg, 1.48 mmol), water (10 mL) and tetrahydrofuran (10 mL). Add lithium hydroxide monohydrate (0.22 g, 5.18 mmol) and stir at room temperature for 24 hours. Heat to reflux for 5 hours then pour into 1N hydrochloric acid (100 mL). Extract into ethyl acetate, dry (MgSO4) and evaporate the solvent in vacuo to give the crude product (0.72 g) as a white solid. Recrystallize (ethyl acetate/hexane) to give the title compound (0.32 g, 57%); mp 254°-6° C.

Workup

  1. temperatureHeat
  2. temperatureto reflux for 5 hours
  3. extractionExtract into ethyl acetate
  4. dry with materialdry (MgSO4)
  5. customevaporate the solvent in vacuo
  6. customto give the crude product (0.72 g) as a white solid
  7. customRecrystallize (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-a304f90826de418f904d28a58df431a9
Source dataset
uspto-grants-1993_02
Patent number
US05189054

Reaction notes

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