Potassium Hydroxide → HCID 23291945, compound

HRID 365516Notes

Reaction equation

HRID 365516 reaction equation
[CH:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([N:14]([CH2:26][CH2:27][CH:28]([CH3:30])[CH3:29])[C:15]3[CH:25]=[CH:24][C:18]([C:19]([O:21]CC)=[O:20])=[CH:17][CH:16]=3)=[CH:11][CH:12]=2)[C:7]([CH3:32])([CH3:31])[CH2:6][CH2:5]1)([CH3:3])[CH3:2].[OH-].[K+]>C(O)C>[CH:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([N:14]([CH2:26][CH2:27][CH:28]([CH3:30])[CH3:29])[C:15]3[CH:16]=[CH:17][C:18]([C:19]([OH:21])=[O:20])=[CH:24][CH:25]=3)=[CH:11][CH:12]=2)[C:7]([CH3:32])([CH3:31])[CH2:6][CH2:5]1)([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 23291924HCID 23291924, compound2×

Product 1

HCID 23291945HCID 23291945, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
40 °C

Procedure

Ethyl 4-[(1-isopropyl-4,4-dimethyl-1,2,3,4-tetrahydroquinolin-6-yl) (3-methylbutyl)amino]benzoate (Compound 13, 20 mg, 0.05 mmol) was dissolved in ethanol (4.0 mL) and the solution treated with 1.4 M KOH (1.0 mL). The solution was heated to 40° C. and stirred for 24 hours. The solution was cooled and concentrated under reduced pressure. The residue was diluted with water, acidified with 10% HCl, and extracted with ethyl acetate (2×). The combined organic layers were washed with brine, dried (MgSO4), filtered and concentrated under reduced pressure to give the title compound (15 mg, 79%) as a solid.

Workup

  1. temperatureThe solution was cooled
  2. concentrationconcentrated under reduced pressure
  3. additionThe residue was diluted with water
  4. extractionextracted with ethyl acetate (2×)
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-2e579b513a4543ff8313808f71a49f2f
Source dataset
uspto-grants-2000_10
Patent number
US06127382

Reaction notes

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