Lithium hydroxide, monohydrate → HCID 57030474, compound

HRID 2082519Notes

Reaction equation

HRID 2082519 reaction equation
[CH2:1]([C:8]1[CH:34]=[CH:33][CH:32]=[CH:31][C:9]=1[C:10](=[O:30])[CH2:11][CH2:12][NH:13][C:14]1[C:22]2[C:17](=[CH:18][C:19]([Cl:24])=[CH:20][C:21]=2[Cl:23])[NH:16][C:15]=1[C:25]([O:27]CC)=[O:26])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.[OH-].[Li+]>O1CCCC1.O>[CH2:1]([C:8]1[CH:34]=[CH:33][CH:32]=[CH:31][C:9]=1[C:10](=[O:30])[CH2:11][CH2:12][NH:13][C:14]1[C:22]2[C:17](=[CH:18][C:19]([Cl:24])=[CH:20][C:21]=2[Cl:23])[NH:16][C:15]=1[C:25]([OH:27])=[O:26])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrate3×HCID 57281946HCID 57281946, compound

Product 1

HCID 57030474HCID 57030474, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
60 °C

Procedure

Dissolve 3-[(2-benzylphenacyl)methylamino]-2-carbethoxy-4,6-dichloroindole (200 mg, 0.41 mmol) in tetrahydrofuran (3 mL) and add water (3 mL). Add lithium hydroxide monohydrate (1.2 mmol) and heat at 60° C. overnight. Add addition lithium hydroxide monohydrate (1.2 mmol) and heat at 60° C. for 5 hours. Allow some of the tetrahydrofuran to evaporate and add methanol to form a homogeneous solution. Heat for 3 days, adding additional lithium hydroxide monohydrate (2.4 mmol). Dilute with water and filter. Acidify, extract into ethyl acetate and dry (MgSO4). Evaporate the solvent in vacuo and recrystallize (ethyl acetate/hexane) to give the title compound as a white powder (180 mg, 97%); mp 280°-83° C.

Workup

  1. additionAdd
  2. customto evaporate
  3. additionadd methanol
  4. customto form a homogeneous solution
  5. temperatureHeat for 3 days
  6. filtrationfilter
  7. extractionAcidify, extract into ethyl acetate
  8. dry with materialdry (MgSO4)
  9. customEvaporate the solvent in vacuo
  10. customrecrystallize (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-2e936a9fda004dcb9e6c91552185980d
Source dataset
uspto-grants-1993_02
Patent number
US05189054

Reaction notes

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