Potassium Hydroxide → HCID 9820541, compound

HRID 365540Notes

Reaction equation

C([O:3][C:4](=[O:29])[C:5]1[CH:10]=[CH:9][C:8]([N:11]([C:13]2[CH:22]=[C:21]3[C:16]([C:17]([CH3:27])([CH3:26])[CH2:18][CH2:19][N:20]3[CH:23]([CH3:25])[CH3:24])=[CH:15][C:14]=2[CH3:28])[CH3:12])=[CH:7][CH:6]=1)C.[OH-].[K+]>C(O)C>[CH:23]([N:20]1[C:21]2[C:16](=[CH:15][C:14]([CH3:28])=[C:13]([N:11]([CH3:12])[C:8]3[CH:7]=[CH:6][C:5]([C:4]([OH:29])=[O:3])=[CH:10][CH:9]=3)[CH:22]=2)[C:17]([CH3:27])([CH3:26])[CH2:18][CH2:19]1)([CH3:25])[CH3:24]

Participants

Conditions

Temperature: 50 °C

Procedure

A solution of 4-[(1-isopropyl-4,4,6-trimethyl-1,2,3,4-tetrahydroquinolin-7-yl)-methyl-amino]-benzoic acid ethyl ester (Compound 47, 8.9 mg, 0.02256 mmol) in ethanol (1 mL) was treated with 2N KOH (0.5 mL) and stirred at 50° C. for 18 hours. 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 (50% ethyl acetate in hexane, Rf=0.22) to give the title compound (7 mg, 85%) as a white 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 (50% ethyl acetate in hexane, Rf=0.22)

Sources & evidence

ORD record: ord-53e9383a844345f2ba3e5386eb1e601f
Source dataset: uspto-grants-2000_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06127382

Reaction notes

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