Potassium Hydroxide → HCID 23291908, compound
Reaction equation
[CH:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([CH2:14][NH:15][C:16]3[CH:26]=[CH:25][C:19]([C:20]([O:22]CC)=[O:21])=[CH:18][CH:17]=3)=[CH:11][CH:12]=2)[C:7]([CH3:28])([CH3:27])[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]([CH2:14][NH:15][C:16]3[CH:17]=[CH:18][C:19]([C:20]([OH:22])=[O:21])=[CH:25][CH:26]=3)=[CH:11][CH:12]=2)[C:7]([CH3:28])([CH3:27])[CH2:6][CH2:5]1)([CH3:3])[CH3:2]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 40 °C
Procedure
Ethyl 4-[(1-isopropyl-4,4-dimethyl-1,2,3,4-tetrahydroquinolin-6-yl)methylamino]benzoate (Compound 9, 43 mg, 0.11 mmol) was dissolved in ethanol (4.0 mL) and the solution treated with 2.3 M KOH (1.0 mL). The solution was heated to 40° C. and stirred for 16 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. Purification by silica gel chromatography (30% ethyl acetate in hexanes) give the title compound (29 mg, 73%) as a solid.
Workup
- temperatureThe solution was cooled
- concentrationconcentrated under reduced pressure
- additionThe residue was diluted with water
- extractionextracted with ethyl acetate (2×)
- washThe combined organic layers were washed with brine
- dry with materialdried (MgSO4)
- filtrationfiltered
- concentrationconcentrated under reduced pressure
- customPurification by silica gel chromatography (30% ethyl acetate in hexanes)
Sources & evidence
- ORD record
- ord-35c7faf1d8464d74bf899884f0f24d97
- Source dataset
- uspto-grants-2000_10
- Patent number
- US06127382
Reaction notes
Loading…