Acetone Cyanohydrin → HCID 178481541, compound

HRID 2194488Notes

Reaction equation

HRID 2194488 reaction equation
[CH3:1][N:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][N:10]=2)[CH:5]=[C:4]([C:12]([O:14]C2CCCC(=O)C=2)=O)[C:3]1=[O:22].[CH2:23](N(CC)CC)[CH3:24].C[C:31]([CH3:35])([OH:34])[C:32]#N.[C:36](=[O:39])([O-])O.[Na+]>C(#N)C>[OH:39][C:36]1[CH2:24][CH2:23][CH2:35][C:31](=[O:34])[C:32]=1[C:12]([C:4]1[C:3](=[O:22])[N:2]([CH3:1])[C:11]2[C:6]([CH:5]=1)=[CH:7][CH:8]=[CH:9][N:10]=2)=[O:14]

Participants

6

Reactant 4

HCID 6406Acetone CyanohydrinHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 67009789HCID 67009789, compound

Product 1

HCID 178481541HCID 178481541, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

0.83 g (2.8 mmol) of 3-oxo-1-cyclohexenyl 1-methyl-2-oxo-1,2-dihydro-1,8-naphthyridine-3-carboxylate was dissolved in acetonitrile (50 mL). 0.43 mL (3.1 mmol) of triethylamine and 0.26 g (3.1 mmol) of acetone cyanohydrin were added to the above solution, and 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. The residue was purified by column chromatography (ethyl acetate:n-hexane=1:1 to 1:0), and thus, 0.30 g of the title compound was obtained as a pale yellow powder (yield: 36%).

Workup

  1. washthe mixture was washed with ethyl acetate
  2. additionCitric acid was added to the aqueous phase
  3. extractionthe reaction mixture was extracted with ethyl acetate
  4. washThe organic phase was washed with water
  5. customdried
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography (ethyl acetate:n-hexane=1:1 to 1:0)

Sources & evidence

ORD record
ord-e37d3205edcd413d99af76aaf6653256
Source dataset
uspto-grants-2012_12
Patent number
US08334236B2

Reaction notes

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