Citric Acid → HCID 178516091, compound

HRID 2194496Notes

Reaction equation

HRID 2194496 reaction equation
[C:1]1([N:7]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][N:15]=3)[CH:10]=[C:9]([C:17](OC3CCCC(=O)C=3)=[O:18])[C:8]2=[O:27])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.C[C:36]([CH3:40])([OH:39])[C:37]#N.[C:41](O)(=O)[CH2:42][C:43](CC(O)=O)(C(O)=O)[OH:44]>ClCCl>[OH:44][C:43]1[CH2:42][CH2:41][CH2:40][C:36](=[O:39])[C:37]=1[C:17]([C:9]1[C:8](=[O:27])[N:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[C:16]2[C:11]([CH:10]=1)=[CH:12][CH:13]=[CH:14][N:15]=2)=[O:18]

Participants

6

Reactant 4

HCID 311Citric AcidHCID 6406Acetone CyanohydrinHCID 8471TriethylamineHCID 67009653HCID 67009653, compound

Product 1

HCID 178516091HCID 178516091, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2.16 g (6.0 mmol) of 3-oxo-1-cyclohexenyl 1-phenyl-2-oxo-1,2-dihydro-1,8-naphthyridine-3-carboxylate was dissolved in dichloromethane (50 mL), and 1.01 mL (7.2 mmol) of triethylamine and 0.56 g (6.6 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 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 washed with methanol, and thus 1.01 g (yield: 47%) of the title compound was obtained as pale brown crystals.

Workup

  1. extractionthe mixture was extracted with dichloromethane
  2. washThe organic phase was washed with water
  3. customdried
  4. concentrationconcentrated
  5. washThe residue was washed with methanol

Sources & evidence

ORD record
ord-df8c6854539b4d50ac7f0a2074ad63e8
Source dataset
uspto-grants-2012_12
Patent number
US08334236B2

Reaction notes

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