Citric Acid → HCID 178516092, compound

HRID 2194492Notes

Reaction equation

HRID 2194492 reaction equation
[CH2:1]([N:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][N:16]=2)[CH:11]=[C:10]([C:18](OC2CCCC(=O)C=2)=[O:19])[C:9]1=[O:28])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.C[C:37]([CH3:41])([OH:40])[C:38]#N.[C:42](O)(=O)[CH2:43][C:44](CC(O)=O)(C(O)=O)[OH:45]>ClCCl>[CH2:1]([N:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][N:16]=2)[CH:11]=[C:10]([C:18]([C:38]2[C:44](=[O:45])[CH2:43][CH2:42][CH2:41][C:37]=2[OH:40])=[O:19])[C:9]1=[O:28])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 311Citric AcidHCID 6406Acetone CyanohydrinHCID 8471TriethylamineHCID 67009737HCID 67009737, compound

Product 1

HCID 178516092HCID 178516092, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2.13 g (5.7 mmol) of 3-oxo-1-cyclohexenyl 1-benzyl-2-oxo-1,2-dihydro-1,8-naphthyridine-3-carboxylate was dissolved in dichloromethane (60 mL), and 0.97 mL (6.9 mmol) of triethylamine and 0.54 g (6.3 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 1.31 g of the title compound was obtained as dark yellow crystals (yield: 62%).

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-cafdfca64dd742c88f785afdcd051ddb
Source dataset
uspto-grants-2012_12
Patent number
US08334236B2

Reaction notes

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