Ethanol → HCID 57002188, compound

HRID 365522Notes

Reaction equation

[CH:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([CH2:15][CH2:16][NH:17][C:18]3[CH:28]=[CH:27]C=C[C:19]=3[C:20](OCC)=O)=[C:11]([CH3:14])[CH:12]=2)[C:7]([CH3:30])([CH3:29])[CH2:6][CH2:5]1)([CH3:3])[CH3:2].[OH-:31].[K+].[CH2:33]([OH:35])[CH3:34]>>[CH:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([CH2:15][CH2:16][NH:17][C:18]3[CH:28]=[CH:27][C:34]([C:33]([OH:31])=[O:35])=[CH:20][CH:19]=3)=[C:11]([CH3:14])[CH:12]=2)[C:7]([CH3:30])([CH3:29])[CH2:6][CH2:5]1)([CH3:2])[CH3:3]

Participants

Reactant 3

HCID 702Ethanol

HCID 14797Potassium Hydroxide

HCID 86755924HCID 86755924, compound2×

Product 1

HCID 57002188HCID 57002188, compound

Conditions

Temperature: 40 °C

Procedure

Ethyl [(1-isopropyl-4,4,7-trimethyl-1,2,3,4-tetrahydroquinolin-6-yl)ethylamino]benzoate (Compound 23, 0.16 g, 0.39 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 20 hours. The solution was cooled and concentrated under reduced pressure. The residue was diluted with water, acidified with 10% HCl, sat. ammonium chloride, 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 (115 mg, 77%) as light yellow crystals.

Workup

temperatureThe solution was cooled
concentrationconcentrated under reduced pressure
additionThe residue was diluted with water
extractionextracted with ether (2×)
washThe combined organic layers were washed with brine
dry with materialdried (MgSO4)
filtrationfiltered
concentrationconcentrated under reduced pressure
customPurification
customby recrystallization in ethanol
customgave (115 mg, 77%) as light yellow crystals

Sources & evidence

ORD record: ord-d2ff1142d789454d96813e47f8524c23
Source dataset: uspto-grants-2000_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06127382

Reaction notes

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