Potassium Carbonate → 4,4-Dimethyl-1,2,3,4-tetrahydro-N-(4-methylphenyl)-7-ethynylquinoline

HRID 1598961Notes

Reaction equation

[CH3:1][C:2]1([CH3:25])[C:11]2[C:6](=[CH:7][C:8]([C:12]#[C:13][Si](C)(C)C)=[CH:9][CH:10]=2)[N:5]([C:18]2[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][CH:19]=2)[CH2:4][CH2:3]1.C(=O)([O-])[O-].[K+].[K+]>CO.O1CCCC1>[CH3:1][C:2]1([CH3:25])[C:11]2[C:6](=[CH:7][C:8]([C:12]#[CH:13])=[CH:9][CH:10]=2)[N:5]([C:18]2[CH:19]=[CH:20][C:21]([CH3:24])=[CH:22][CH:23]=2)[CH2:4][CH2:3]1

Participants

Conditions

Temperature: 30 °C

Procedure

To a solution of 0.18 g (0.52 mmol) of 4,4-dimethyl-1,2,3,4-tetrahydro-N-(4-methylphenyl)-7-[2-(trimethylsilyl)ethynyl]quinoline (Compound 2) in 12.0 mL of methanol and 1.0 mL of tetrahydrofuran was added 0.088 g (0.64 mmol) of potassium carbonate, and the resulting mixture was stirred at room temperature for 6 hours and at 30° C. for 1 hour. The mixture was concentrated in vacuo, water was added, and the mixture was extracted with diethyl ether (2x). The combined organic layers were washed with brine, dried (MgSO4), filtered, and concentrated in vacuo to give the title compound as an orange oil. PNMR (300 MHz, CDCl3): d 1.34 (6 H, s), 1.83 (2 H, t, J=6.0 Hz), 2.35 (3 H, s), 2.86 (1 H, s), 3.56 (2 H, t, J=6.0 Hz), 6.73 (1 H, d, J=1.6 Hz), 6.82 (1 H, dd, J=7.9, 1.6 Hz), 7.11 (2 H, d, J=8.4 Hz), 7.17 (1 H, J=7.9 Hz), 7.18 (2 H, d, J=8.4 Hz).

Workup

concentrationThe mixture was concentrated in vacuo, water
additionwas added
extractionthe mixture was extracted with diethyl ether (2x)
washThe combined organic layers were washed with brine
dry with materialdried (MgSO4)
filtrationfiltered
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-e31c0bdfa057405f9d9f2a16e192b9ac
Source dataset: uspto-grants-1998_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05739338

Reaction notes

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