Potassium Carbonate → HCID 59441858, compound

HRID 1014380Notes

Reaction equation

[CH3:1][C:2]1([CH3:17])[C:11]2[C:6](=[CH:7][C:8]([N+:14]([O-:16])=[O:15])=[C:9]([O:12][CH3:13])[CH:10]=2)[NH:5][CH2:4][CH2:3]1.C(=O)([O-])[O-].[K+].[K+].[Br:24][CH2:25][C:26](Cl)=[O:27]>O1CCCC1>[Br:24][CH2:25][C:26]([N:5]1[C:6]2[C:11](=[CH:10][C:9]([O:12][CH3:13])=[C:8]([N+:14]([O-:16])=[O:15])[CH:7]=2)[C:2]([CH3:17])([CH3:1])[CH2:3][CH2:4]1)=[O:27]

Participants

Conditions

Temperature: 0 °C

Procedure

4,4-dimethyl-6-(methyloxy)-7-nitro-1,2,3,4-tetrahydroquinoline (1.32 g, 5.59 mmol) was dissolved in tetrahydrofuran (50 mL). This solution was treated with potassium carbonate (1.54 g, 11.2 mmol, Aldrich) and cooled to 0° C. Bromoacetyl chloride (0.93 mL, 11 mmol, Fluka) was added (white precipitation observed) and the reaction stirred for 15 min. The reaction mixture was then diluted with water and extracted with ethyl acetate. The organic layer was dried over magnesium sulfate, filtered, and concentrated to give 1-(bromoacetyl)-4,4-dimethyl-6-(methyloxy)-7-nitro-1,2,3,4-tetrahydroquinoline (assumed 5.59 mmol, 100%). This material was analyzed by 1H NMR (amide rotomers were observed) and taken to bromide displacement reactions directly without further purification. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.33 (s, 6 H), 1.75-1.86 (m, 2 H), 3.72-3.82 (m, 2 H), 3.95 (s, 3 H), 4.31-4.69 (two singles at 4.37 and 4.63, 2 H), 7.27 (s, 1 H), 8.28 (very broad singlet, 1 H).

Workup

custom(white precipitation observed)
additionThe reaction mixture was then diluted with water
extractionextracted with ethyl acetate
dry with materialThe organic layer was dried over magnesium sulfate
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-679b10018afe4f7d8ae633d91a6edcf0
Source dataset: uspto-grants-2011_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07981903B2

Reaction notes

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