Potassium Hydroxide → HCID 70279156, compound

HRID 365530Notes

Reaction equation

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

Participants

Conditions

Temperature: 50 °C

Procedure

A solution ethyl 4-[(1-isopropyl-4,4-dimethyl-1,2,3,4-tetrahydroquinolin-7-yl)ethylamino]-benzoate (Compound 35, 5.6 mg, 0.0142 mmol) of 7 in ethanol (1 mL) was treated with 2N KOH (0.5 mL) and stirred at 50° C. for 2 days. The solvent was removed under reduced pressure and the residue was washed with ethyl acetate and acidified with 2N HCl. The aqueous layer was extracted with ethyl acetate and the combined organic layers were dried with MgSO4, filtered, and concentrated under reduced pressure. The residue was purified by silica gel chromatography (20% ethyl acetate in hexane, Rf=0.11) to give the title compound (5.2 mg, quant.) as a pale yellow solid:

Workup

customThe solvent was removed under reduced pressure
washthe residue was washed with ethyl acetate
extractionThe aqueous layer was extracted with ethyl acetate
dry with materialthe combined organic layers were dried with MgSO4
filtrationfiltered
concentrationconcentrated under reduced pressure
customThe residue was purified by silica gel chromatography (20% ethyl acetate in hexane, Rf=0.11)

Sources & evidence

ORD record: ord-5f66bc66fd5448d4a0f573eef31814be
Source dataset: uspto-grants-2000_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06127382

Reaction notes

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