Potassium Hydroxide → HCID 178427855, compound

HRID 402731Notes

Reaction equation

HRID 402731 reaction equation
[NH:1]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[C:3]([CH:10]=[C:11]2[O:15][C:14]([NH:16][C:17]3[CH:22]=[CH:21][C:20]([F:23])=[CH:19][C:18]=3[CH3:24])=[C:13](C(OCC)=O)[C:12]2=[O:30])=[CH:2]1.[OH-].[K+]>C(O)C>[NH:1]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[C:3]([CH:10]=[C:11]2[C:12](=[O:30])[CH:13]=[C:14]([NH:16][C:17]3[CH:22]=[CH:21][C:20]([F:23])=[CH:19][C:18]=3[CH3:24])[O:15]2)=[CH:2]1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 178469555HCID 178469555, compound

Product 1

HCID 178427855HCID 178427855, compoundYield 96.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of the compound (0.15 g, 0.37 mmol) of Example 97 in ethanol (4.0 mL), 50% potassium hydroxide solution (2.0 mL, 0.036 mol) was added at ambient temperature. The mixture was refluxed for 2 h. Cooled to ambient temperature, the solvent was removed under reduced pressure. Water was added to this residue, the mixture was washed with ethyl acetate then 1M hydrochloric acid was added to adjust pH to acidic. The precipitate was collected by filtration, washed with water, diethyl ether, ethyl acetate and hexane then dried to afford the titled compound as solid (0.12 g, y. 93%).

Workup

  1. temperatureThe mixture was refluxed for 2 h
  2. customthe solvent was removed under reduced pressure
  3. additionWater was added to this residue
  4. washthe mixture was washed with ethyl acetate
  5. addition1M hydrochloric acid was added
  6. filtrationThe precipitate was collected by filtration
  7. washwashed with water, diethyl ether, ethyl acetate and hexane
  8. customthen dried

Sources & evidence

ORD record
ord-dbfe042f3b414ae082c6e3821dbac063
Source dataset
uspto-grants-2014_06
Patent number
US08742113B2

Reaction notes

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