Methylamine → HCID 70896054, compound

HRID 2403696Notes

Reaction equation

[CH2:1]([O:3][C:4]([C:6]1[CH:15]=[C:14]2[C:9]([CH:10]=[CH:11][CH:12]=[N+:13]2[O-])=[CH:8][CH:7]=1)=[O:5])[CH3:2].FC(F)(F)S(OS(C(F)(F)F)(=O)=O)(=O)=O.[CH3:32][NH2:33].O1CCCC1>ClCCl>[CH3:32][NH:33][C:12]1[CH:11]=[CH:10][C:9]2[C:14](=[CH:15][C:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])=[CH:7][CH:8]=2)[N:13]=1

Participants

Conditions

Temperature: -70 °C

Procedure

To a −70° C. solution of 7-(ethoxycarbonyl)quinoline 1-oxide (1.67 g, 7.70 mmol) in dichloromethane (80 mL) was added trifluoromethanesulfonic anhydride (1.43 mL, 8.47 mmol) dropwise, under a nitrogen atmosphere. The mixture was stirred at −70° C. for 5 minutes. Then a solution of methylamine in tetrahydrofuran (21 mL, 42 mmol, 2.0 M) was added dropwise at −70° C. The mixture was stirred for 5 minutes and then the reaction was quenched with water (20 mL). The layers were separated and the aqueous was extracted with dichloromethane (3×30 mL). The combined organics were washed with brine, dried over sodium sulfate, filtered, and concentrated. Purification by flash column chromatography gave the title compound (720 mg, 41%) as a yellow solid. 1H NMR (400 MHz, CDCl3, δ): 8.42 (s, 1 H), 7.84-7.82 (m, 2 H), 7.63-7.61 (m, 1 H), 6.72-6.70 (m, 1 H), 4.92 (br. s., 1 H), 4.44-4.38 (m, 2 H), 3.12-3.11 (m, 3 H), 1.44-1.40 (m, 3 H).

Workup

stirringThe mixture was stirred for 5 minutes
customthe reaction was quenched with water (20 mL)
customThe layers were separated
extractionthe aqueous was extracted with dichloromethane (3×30 mL)
washThe combined organics were washed with brine
dry with materialdried over sodium sulfate
filtrationfiltered
concentrationconcentrated
customPurification by flash column chromatography

Sources & evidence

ORD record: ord-1bf86d425c58449e874978bc8ba2d2f9
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08802688B2

Reaction notes

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