Dimethylamine → N,N-dimethyl-3-[6-(methyloxy)-7-nitro-3,4-dihydro-1(2H)-quinolinyl]-3-oxo-1-propanamine
Reaction equation
[C:1]([N:5]1[C:14]2[C:9](=[CH:10][C:11]([O:18][CH3:19])=[C:12]([N+:15]([O-:17])=[O:16])[CH:13]=2)[CH2:8][CH2:7][CH2:6]1)(=[O:4])[CH:2]=[CH2:3].[CH3:20][NH:21][CH3:22]>CO>[CH3:20][N:21]([CH3:22])[CH2:3][CH2:2][C:1]([N:5]1[C:14]2[C:9](=[CH:10][C:11]([O:18][CH3:19])=[C:12]([N+:15]([O-:17])=[O:16])[CH:13]=2)[CH2:8][CH2:7][CH2:6]1)=[O:4]Participants
Conditions
- Temperature
- 65 °C
Procedure
1-acryloyl-6-(methyloxy)-7-nitro-1,2,3,4-tetrahydroquinoline (crude from previous reaction, assumed 0.91 mmol) was dissolved in methanol (5 mL), treated with excess dimethyl amine (5.0 mL, 10 mmol, 2 M in THF, Aldrich), and the reaction heated in a sealed tube at 65° C. for 16 h. The mixture was cooled, concentrated, and partitioned between ethyl acetate and saturated aqueous sodium bicarbonate. The aqueous layer was separated and then back-extracted with dichloromethane. The organic layers were combined, dried over magnesium sulfate, filtered, and concentrated to give N,N-dimethyl-3-[6-(methyloxy)-7-nitro-3,4-dihydro-1(2H)-quinolinyl]-3-oxo-1-propanamine which was taken directly to the next step without determination of yield. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.83-1.94 (m, 2 H), 2.18 (bs, 6 H), 2.56-2.71 (m, 4 H), 2.80 (t, J=6.4 Hz, 2 H), 3.71 (t, J=6.0 Hz, 2 H), 3.90 (s, 3 H), 7.20 (s, 1 H), 8.27 (very broad singlet due to amide rotomers, 1 H); ESIMS (M+H)+=308.
Workup
- temperatureThe mixture was cooled
- concentrationconcentrated
- custompartitioned between ethyl acetate and saturated aqueous sodium bicarbonate
- customThe aqueous layer was separated
- extractionback-extracted with dichloromethane
- dry with materialdried over magnesium sulfate
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-1071cd8b86c64c919c8bac6127b07390
- Source dataset
- uspto-grants-2011_07
- Patent number
- US07981903B2
Reaction notes
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