Citric Acid → HCID 178492037, compound

HRID 2194499Notes

Reaction equation

HRID 2194499 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6]([N:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][N:17]=3)[CH:12]=[C:11]([C:19](OC3CCCC(=O)C=3)=[O:20])[C:10]2=[O:29])=[CH:5][CH:4]=1.C(N(CC)CC)C.C[C:38]([CH3:42])([OH:41])[C:39]#N.[C:43](O)(=O)[CH2:44][C:45](CC(O)=O)(C(O)=O)[OH:46]>ClCCl>[OH:46][C:45]1[CH2:44][CH2:43][CH2:42][C:38](=[O:41])[C:39]=1[C:19]([C:11]1[C:10](=[O:29])[N:9]([C:6]2[CH:7]=[N:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[C:18]2[C:13]([CH:12]=1)=[CH:14][CH:15]=[CH:16][N:17]=2)=[O:20]

Participants

6

Reactant 4

HCID 311Citric AcidHCID 6406Acetone CyanohydrinHCID 8471TriethylamineHCID 67010384HCID 67010384, compound

Product 1

HCID 178492037HCID 178492037, compoundYield 21%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1.78 g (4.5 mmol) of 3-oxo-1-cyclohexenyl 1-(6-methoxy-3-pyridyl)-2-oxo-1,2-dihydro-1,8-naphthyridine-3-carboxylate was dissolved in dichloromethane (50 mL), and 0.77 mL (5.5 mmol) of triethylamine and 0.43 g (5.0 mmol) of acetone cyanohydrin were added to the above solution. The resulting mixture was stirred overnight at room temperature. The reaction mixture was poured into an aqueous solution of citric acid, and the mixture was extracted with dichloromethane. The organic phase was washed with water, dried, and concentrated. The residue was purified by column chromatography (ethyl acetate:n-hexane=1:1 to 7:3), and thus 0.37 g (yield: 21%) of the title compound was obtained as orange-colored crystals.

Workup

  1. extractionthe mixture was extracted with dichloromethane
  2. washThe organic phase was washed with water
  3. customdried
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography (ethyl acetate:n-hexane=1:1 to 7:3)

Sources & evidence

ORD record
ord-ce2373898b414b3a9fec1ad0dc72564c
Source dataset
uspto-grants-2012_12
Patent number
US08334236B2

Reaction notes

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