Lithium Hydroxide → HCID 58277417, compound

HRID 1949234Notes

Reaction equation

HRID 1949234 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:8]2[C:12]([C:13]3[CH:18]=[CH:17][C:16]([F:19])=[C:15]([C:20]([F:23])([F:22])[F:21])[CH:14]=3)=[CH:11][C:10]([C:24]([O:26]CC)=[O:25])=[N:9]2)[CH:5]=[CH:6][CH:7]=1.[OH-].[Li+]>O1CCOCC1.O>[Cl:1][C:2]1[CH:3]=[C:4]([N:8]2[C:12]([C:13]3[CH:18]=[CH:17][C:16]([F:19])=[C:15]([C:20]([F:22])([F:23])[F:21])[CH:14]=3)=[CH:11][C:10]([C:24]([OH:26])=[O:25])=[N:9]2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 58277455HCID 58277455, compound

Product 1

HCID 58277417HCID 58277417, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

3.60 g (8.72 mmol) of the compound of Example 27A are provided in 50 ml of 1,4-dioxane, 50 ml (50 mmol) of a 1N solution of lithium hydroxide in water are added, and the mixture is heated under reflux for 1 h. The mixture is concentrated, the residue is diluted with water, a conc. aqueous hydrogen chloride solution is subsequently added until the pH is acidic, the mixture is extracted with ethyl acetate, and the organic phase is dried over magnesium sulfate, filtered and concentrated. 3.30 g (98% of theory) of the title compound are obtained.

Workup

  1. temperaturethe mixture is heated
  2. temperatureunder reflux for 1 h
  3. concentrationThe mixture is concentrated
  4. additionthe residue is diluted with water
  5. additiona conc. aqueous hydrogen chloride solution is subsequently added until the pH
  6. extractionthe mixture is extracted with ethyl acetate
  7. dry with materialthe organic phase is dried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-a5d98e00d8bc4a9d9f381666a1a8d71c
Source dataset
uspto-grants-2013_03
Patent number
US08399682B2

Reaction notes

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