Acetone Cyanohydrin → HCID 178481540, compound
Reaction equation
[CH3:1][N:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]([F:15])([F:14])[F:13])[N:10]=2)[CH:5]=[C:4]([C:16](OC2CCCC(=O)C=2)=[O:17])[C:3]1=[O:26].[CH2:27](N(CC)CC)[CH3:28].C[C:35]([CH3:39])([OH:38])[C:36]#N.[C:40](=[O:43])([O-])O.[Na+]>C(#N)C>[OH:43][C:40]1[CH2:28][CH2:27][CH2:39][C:35](=[O:38])[C:36]=1[C:16]([C:4]1[C:3](=[O:26])[N:2]([CH3:1])[C:11]2[C:6]([CH:5]=1)=[CH:7][CH:8]=[C:9]([C:12]([F:15])([F:14])[F:13])[N:10]=2)=[O:17]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
0.51 g (1.4 mmol) of 3-oxo-1-cyclohexenyl 1-methyl-2-oxo-7-(trifluoromethyl)-1,2-dihydro-1,8-naphthyridine-3-carboxylate was dissolved in acetonitrile (50 mL), and 0.15 g (1.5 mmol) of triethylamine and 0.14 g (1.6 mmol) of acetone cyanohydrin were added to the above solution. The resulting mixture was stirred for one whole day and night at room temperature. The reaction mixture was poured into a saturated aqueous solution of sodium hydrogen carbonate, and the mixture was washed with ethyl acetate. Citric acid was added to the aqueous phase to adjust the aqueous phase to pH 3 to 4, and the reaction mixture was extracted with ethyl acetate. The organic phase was washed with water, dried, and concentrated, and the residue was washed with diisopropyl ether. Thus, 0.17 g (yield: 33%) of the title compound was obtained as light brown crystals.
Workup
- washthe mixture was washed with ethyl acetate
- additionCitric acid was added to the aqueous phase
- extractionthe reaction mixture was extracted with ethyl acetate
- washThe organic phase was washed with water
- customdried
- concentrationconcentrated
- washthe residue was washed with diisopropyl ether
Sources & evidence
- ORD record
- ord-3b3da323c09f46af9d849b6a8b3928fd
- Source dataset
- uspto-grants-2012_12
- Patent number
- US08334236B2
Reaction notes
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