Acetamide → N-(6-Methyl-2-quinolinyl)acetamide

HRID 1503153Notes

Reaction equation

Cl[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([CH3:12])[CH:8]=2)[N:3]=1.[C:13]([NH2:16])(=[O:15])[CH3:14].C([O-])([O-])=O.[K+].[K+]>O>[C:13]([NH:16][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([CH3:12])[CH:8]=2)[N:3]=1)(=[O:15])[CH3:14]

Participants

Conditions

Temperature: 230 °C

Procedure

Chloride 44 (0.300 g, 1.69 mmol) was diluted with molten anhydrous acetamide (8 g, 135 mmol), and K2CO3 (1.17 g, 8.45 mmol) was added. The mixture was heated in a sand bath, at reflux (˜230° C.) for 16 h. The mixture was cooled, poured into H2O (120 mL) and extracted with EtOAc (4×30 mL). The organic layers were washed with H2O (3×100 mL) and sat. aq. NaCl (50 mL) and dried over anhydrous sodium sulfate and concentrated. Purification of the residue by flash column chromatography (SiO2), eluting with a gradient of 10% EtOAc in CH2Cl2 to 30% EtOAc in CH2Cl2 afforded the desired compound as a white solid (0.250 g, 74%). 1H NMR chemical shifts for this compound are consistent with those reported in the literature. 1H-NMR (500 MHz; CDCl3): δ 8.36 (br d, J=8.6 Hz, 1 H), 8.27 (br s, 1 H), 8.09 (d, J=8.9 Hz, 1 H), 7.70 (d, J=8.6 Hz, 1 H), 7.55 (s, 1 H), 7.50 (dd, J=8.6, 1.9 Hz, 1 H), 2.51 (s, 3 H), 2.24 (s, 3 H).

Workup

additionwas added
temperatureThe mixture was heated in a sand bath
temperatureThe mixture was cooled
extractionextracted with EtOAc (4×30 mL)
washThe organic layers were washed with H2O (3×100 mL) and sat. aq. NaCl (50 mL)
dry with materialdried over anhydrous sodium sulfate
concentrationconcentrated
customPurification of the residue by flash column chromatography (SiO2)
washeluting with a gradient of 10% EtOAc in CH2Cl2 to 30% EtOAc in CH2Cl2

Sources & evidence

ORD record: ord-175d7e59ef24468c90859bbaed6b54f8
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09212144B2

Reaction notes

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