Potassium Hydroxide → HCID 11191324, compound

HRID 1369108Notes

Reaction equation

HRID 1369108 reaction equation
[CH2:1]([N:3]([CH2:31][CH3:32])[CH2:4][CH2:5][N:6]1[C:14]2[C:9](=[C:10]([C:17]([F:20])([F:19])[F:18])[CH:11]=[C:12]([C:15]#[N:16])[CH:13]=2)[C:8]([OH:29])([C:21]2[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][C:22]=2[Cl:28])[C:7]1=[O:30])[CH3:2].[OH-:33].[K+]>C(O)(C)(C)C>[CH2:31]([N:3]([CH2:1][CH3:2])[CH2:4][CH2:5][N:6]1[C:14]2[C:9](=[C:10]([C:17]([F:18])([F:19])[F:20])[CH:11]=[C:12]([C:15](=[O:33])[NH2:16])[CH:13]=2)[C:8]([OH:29])([C:21]2[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][C:22]=2[Cl:28])[C:7]1=[O:30])[CH3:32]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 18518573HCID 18518573, compound

Product 1

HCID 11191324HCID 11191324, compoundYield 75.9%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

To a solution of 1-(2-diethylaminoethyl)-4-trifluoromethyl-6-cyano-3-hydroxy-3-(2,4-dichlorophenyl)oxindole (315 mg, 0.648 mmol) in t-butanol (5 mL) was added powdered KOH (ca. 300 mg) at 50° C. The mixture was stirred for 30 min at the same temperature and passed through a celite pad. The celite was washed with THF and the filtrate was concentrated. The residue was dispersed between water and ethyl acetate and the organic layer was separated. The organic layer was dried over MgSO4 and concentrated to give the title compound (248 mg, 66%). The compound was dissolved in dioxane (2.5 mL) and 4 N HCl in dioxane (0.5 mL) was added. The solvent was evaporated azeotropically with toluene to dryness to give the hydrochloride (331 mg, 94%).

Workup

  1. washThe celite was washed with THF
  2. concentrationthe filtrate was concentrated
  3. additionThe residue was dispersed between water and ethyl acetate
  4. customthe organic layer was separated
  5. dry with materialThe organic layer was dried over MgSO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-b610ce7f91ea49fab3d54e3530923e45
Source dataset
uspto-grants-2003_06
Patent number
US06576656B1

Reaction notes

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