Citric Acid → HCID 178489478, compound

HRID 2194494Notes

Reaction equation

HRID 2194494 reaction equation
[CH3:1][O:2][C:3]1[CH:30]=[CH:29][CH:28]=[CH:27][C:4]=1[CH2:5][N:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][N:14]=2)[CH:9]=[C:8]([C:16](OC2CCCC(=O)C=2)=[O:17])[C:7]1=[O:26].C(N(CC)CC)C.C[C:39]([CH3:43])([OH:42])[C:40]#N.[C:44](O)(=O)[CH2:45][C:46](CC(O)=O)(C(O)=O)[OH:47]>ClCCl>[OH:47][C:46]1[CH2:45][CH2:44][CH2:43][C:39](=[O:42])[C:40]=1[C:16]([C:8]1[C:7](=[O:26])[N:6]([CH2:5][C:4]2[CH:27]=[CH:28][CH:29]=[CH:30][C:3]=2[O:2][CH3:1])[C:15]2[C:10]([CH:9]=1)=[CH:11][CH:12]=[CH:13][N:14]=2)=[O:17]

Participants

6

Reactant 4

HCID 311Citric AcidHCID 6406Acetone CyanohydrinHCID 8471TriethylamineHCID 67009597HCID 67009597, compound

Product 1

HCID 178489478HCID 178489478, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4.82 g (11.9 mmol) of 3-oxo-1-cyclohexenyl 1-(2-methoxybenzyl)-2-oxo-1,2-dihydro-1,8-naphthyridine-3-carboxylate was dissolved in dichloromethane (100 mL), and 2.01 mL (14.3 mmol) of triethylamine and 1.11 g (13.1 mmol) of acetone cyanohydrin were added to the above solution. The 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 purified by column chromatography (ethyl acetate:n-hexane=1:3 to 1:1), and thus 1.59 g (yield: 33%) of the title compound was obtained as yellow 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=1:3 to 1:1)

Sources & evidence

ORD record
ord-2f8f1c6d7b124e1e875ebe9f6b65ece4
Source dataset
uspto-grants-2012_12
Patent number
US08334236B2

Reaction notes

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