Triethylamine → 6-[2-Methoxy-4-(thiophen-2-ylcarbonyloxy)phenyl]-5-(4-methylbenzoyloxymethyl)-2,2,4-trimethyl-1,2-dihydroquinoline

HRID 1043678Notes

Reaction equation

HRID 1043678 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([CH2:21][O:22][C:23](=[O:31])[C:24]3[CH:29]=[CH:28][C:27]([CH3:30])=[CH:26][CH:25]=3)=[C:10]3[C:15](=[CH:16][CH:17]=2)[NH:14][C:13]([CH3:19])([CH3:18])[CH:12]=[C:11]3[CH3:20])=[C:4]([O:32][CH3:33])[CH:3]=1.C(N(CC)CC)C.[C:41]1([C:46](Cl)=[O:47])[S:45][CH:44]=[CH:43][CH:42]=1>C(Cl)Cl>[CH3:33][O:32][C:4]1[CH:3]=[C:2]([O:1][C:46]([C:41]2[S:45][CH:44]=[CH:43][CH:42]=2)=[O:47])[CH:7]=[CH:6][C:5]=1[C:8]1[C:9]([CH2:21][O:22][C:23](=[O:31])[C:24]2[CH:25]=[CH:26][C:27]([CH3:30])=[CH:28][CH:29]=2)=[C:10]2[C:15](=[CH:16][CH:17]=1)[NH:14][C:13]([CH3:19])([CH3:18])[CH:12]=[C:11]2[CH3:20]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 789282-Thiophenecarbonyl chlorideHCID 166606546-(4-Hydroxy-2-methoxyphenyl)-5-(4-methylbenzoyloxymethyl)-2,2,4-trimethyl-1,2-dihydroquinoline

Product 1

HCID 579905846-[2-Methoxy-4-(thiophen-2-ylcarbonyloxy)phenyl]-5-(4-methylbenzoyloxymethyl)-2,2,4-trimethyl-1,2-dihydroquinolineYield 93%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

6-(4-Hydroxy-2-methoxyphenyl)-5-(4-methylbenzoyloxymethyl)-2,2,4-trimethyl-1,2-dihydroquinoline (Reference Compound No. 3-1, 25.6 mg, 0.0577 mmol) was dissolved in anhydrous methylene dichloride (1 mL), and then triethylamine (19 μL, 0.14 mmol) and 2-thenoyl chloride (11.2 mg, 0.0764 mmol) were added thereto. The reaction mixture was stirred at room temperature for 1 hour. The reaction mixture was purified by silica gel column chromatography (hexane-ethyl acetate) to give the titled compound (28.8 mg) as a pale yellow amorphous product. (Yield 93%)

Workup

  1. customThe reaction mixture was purified by silica gel column chromatography (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-172c6aedacff4fdbb248db73d764fc1f
Source dataset
uspto-grants-2013_10
Patent number
US08563551B2

Reaction notes

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