Potassium Hydroxide → HCID 13957693, compound

HRID 2308920Notes

Reaction equation

HRID 2308920 reaction equation
[F:1][CH:2]([F:26])[C:3]1[C:8]([C:9]([O:11]CC)=[O:10])=[C:7]([CH2:14][CH2:15][CH3:16])[C:6]([C:17]([O:19]CC)=[O:18])=[C:5]([C:22]([F:25])([F:24])[F:23])[N:4]=1.[OH-].[K+]>CO>[F:26][CH:2]([F:1])[C:3]1[C:8]([C:9]([OH:11])=[O:10])=[C:7]([CH2:14][CH2:15][CH3:16])[C:6]([C:17]([OH:19])=[O:18])=[C:5]([C:22]([F:25])([F:23])[F:24])[N:4]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 13957668HCID 13957668, compound

Product 1

HCID 13957693HCID 13957693, compoundYield 24.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 20.1 g (0.0525 mole) of the product of Example 13, 11.4 g of 85% KOH, and 100 ml of methanol is held at reflux for 19 hours and concentrated. The residue is treated with 200 ml of water and extracted with ether. The aqueous layer is separated and acidified with 30 ml of concentrated HCl. The oily precipitate is extracted into ether and the ether extract is dried and concentrated. The residue is recrystallized from chloroform to give 4.2 g (24%) of the desired product, m.p. 235.5°-236.5° C.

Workup

  1. temperatureat reflux for 19 hours
  2. concentrationconcentrated
  3. additionThe residue is treated with 200 ml of water
  4. extractionextracted with ether
  5. customThe aqueous layer is separated
  6. extractionThe oily precipitate is extracted into ether
  7. extractionthe ether extract
  8. customis dried
  9. concentrationconcentrated
  10. customThe residue is recrystallized from chloroform

Sources & evidence

ORD record
ord-2b63e8594cfb4e5badfb43e15da204d1
Source dataset
uspto-grants-1987_09
Patent number
US04692184

Reaction notes

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