Pyridine → 2-[4-methyl-2-(3-pyridyl)thiazol-5-yl]-6,7-dihydro-5H-quinolin-8-one oxime
Reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([C:18]2[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=2)[S:5][C:6]=1[C:7]1[CH:16]=[CH:15][C:14]2[CH2:13][CH2:12][CH2:11][C:10](=O)[C:9]=2[N:8]=1.N1C=CC=CC=1.[NH2:30][OH:31].Cl>C(O)C.O>[CH3:1][C:2]1[N:3]=[C:4]([C:18]2[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=2)[S:5][C:6]=1[C:7]1[CH:16]=[CH:15][C:14]2[CH2:13][CH2:12][CH2:11][C:10](=[N:30][OH:31])[C:9]=2[N:8]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Procedure
A solution of 2-[4-methyl-2-(3-pyridyl)thiazol-5-yl]-6,7-dihydro-5H-quinolin-8-one (0.024 g, 0.067 mmol) was dissolved in ethanol (1 mL) and pyridine (0.054 mL, 0.053 g, 0.67 mmol) was added at ambient temperature. To this was added H2N—OH.HCl (0.0070 g, 0.10 mmol) and the resulting yellowish suspension was stirred at ambient temperature monitoring by LCMS. The reaction was complete after 2 hours. The reaction mixture was diluted with water and extracted ethyl acetate. The organic phase was then washed with brine, dried over anhydrous Na2SO4, filtered and concentrated in vacuo. Purification by flash chromatography eluting with a 5 to 10% MeOH: CH2Cl2, gradient gave 13 mg (58%) of the title compound as a yellow solid, and as a single isomer with mp=212-215° C.
Workup
- extractionextracted ethyl acetate
- washThe organic phase was then washed with brine
- dry with materialdried over anhydrous Na2SO4
- filtrationfiltered
- concentrationconcentrated in vacuo
- customPurification by flash chromatography
- washeluting with a 5 to 10% MeOH
Sources & evidence
- ORD record
- ord-e7c6123a450f41279c76f8ff17dfc05c
- Source dataset
- uspto-grants-2015_09
- Patent number
- US09133218B2
Reaction notes
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