Potassium Hydroxide → HCID 23291918, compound

HRID 365521Notes

Reaction equation

HRID 365521 reaction equation
[CH:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([CH2:15][NH:16][C:17]3[CH:27]=[CH:26][C:20]([C:21]([O:23]CC)=[O:22])=[CH:19][CH:18]=3)=[C:11]([CH3:14])[CH:12]=2)[C:7]([CH3:29])([CH3:28])[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]([CH2:15][NH:16][C:17]3[CH:18]=[CH:19][C:20]([C:21]([OH:23])=[O:22])=[CH:26][CH:27]=3)=[C:11]([CH3:14])[CH:12]=2)[C:7]([CH3:29])([CH3:28])[CH2:6][CH2:5]1)([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 23291939HCID 23291939, compound2×

Product 1

HCID 23291918HCID 23291918, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
40 °C

Procedure

Ethyl 4-[(1-isopropyl-4,4,7-trimethyl-1,2,3,4-tetrahydroquinolin-6-yl)methylamino]benzoate (Compound 21, 43 mg, 0.11 mmol) was dissolved in ethanol (4.0 mL) and the solution treated with 1.8 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 ether (2×). The combined organic layers were washed with brine, dried (MgSO4), filtered and concentrated under reduced pressure. Purification by recrystallization in ethanol gave the title compound (25 mg, 63%).

Workup

  1. temperatureThe solution was cooled
  2. concentrationconcentrated under reduced pressure
  3. additionThe residue was diluted with water
  4. extractionextracted with ether (2×)
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customPurification
  10. customby recrystallization in ethanol

Sources & evidence

ORD record
ord-cea8e2af02d24fa6a260517ca79220fa
Source dataset
uspto-grants-2000_10
Patent number
US06127382

Reaction notes

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