Triethylamine → 5-Hydroxymethyl-6-(2-trifluoromethylsulfonyloxyphenyl)-2,2,4-trimethyl-1,2-dihydroquinoline

HRID 1966281Notes

Reaction equation

[OH:1][CH2:2][C:3]1[C:12]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[OH:19])=[CH:11][CH:10]=[C:9]2[C:4]=1[C:5]([CH3:22])=[CH:6][C:7]([CH3:21])([CH3:20])[NH:8]2.C(N(CC)CC)C.[F:30][C:31]([F:37])([F:36])[S:32](Cl)(=[O:34])=[O:33]>ClCCl.C(Cl)(Cl)Cl>[OH:1][CH2:2][C:3]1[C:12]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[O:19][S:32]([C:31]([F:37])([F:36])[F:30])(=[O:34])=[O:33])=[CH:11][CH:10]=[C:9]2[C:4]=1[C:5]([CH3:22])=[CH:6][C:7]([CH3:21])([CH3:20])[NH:8]2

Participants

Conditions

Temperature: 0 °C

Procedure

5-Hydroxymethyl-6-(2-hydroxyphenyl)-2,2,4-trimethyl-1,2-dihydroquinoline (Reference Compound No. 3-1, 293 mg, 0.992 mmol) was dissolved in anhydrous dichloromethane (5 mL) and then triethylamine (167 μL, 1.20 mmol) and trifluoromethanesulfonyl chloride (106 μL, 0.996 mmol) were added thereto at 0° C. After the reaction mixture was stirred at 0° C. for 1 hour, it was diluted with chloroform (20 mL). The whole was washed with saturated aqueous NaHCO3 solution (20 mL) and then the solvent was removed under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate) to give the titled reference compound (177 mg) as an orange solid. (Yield 42%)

Workup

customat 0° C
washThe whole was washed with saturated aqueous NaHCO3 solution (20 mL)
customthe solvent was removed under reduced pressure
customThe obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate)

Sources & evidence

ORD record: ord-9142c59a4b8b492588dbf42d369b923d
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08420635B2

Reaction notes

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