Hydroxyamine hydrochloride → 3-[4-(3-Chlorophenyl)-1-ethyl-7-hydroxyiminomethyl-2-oxo-1,2-dihydro-1,8-naphthyridin-3-yl]propanoic acid

HRID 1582993Notes

Reaction equation

HRID 1582993 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[C:17]3[C:12](=[N:13][C:14]([CH:18]=O)=[CH:15][CH:16]=3)[N:11]([CH2:20][CH3:21])[C:10](=[O:22])[C:9]=2[CH2:23][CH2:24][C:25]([O:27]C)=[O:26])[CH:5]=[CH:6][CH:7]=1.Cl.[NH2:30][OH:31]>O>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[C:17]3[C:12](=[N:13][C:14]([CH:18]=[N:30][OH:31])=[CH:15][CH:16]=3)[N:11]([CH2:20][CH3:21])[C:10](=[O:22])[C:9]=2[CH2:23][CH2:24][C:25]([OH:27])=[O:26])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 22716671Methyl 3-[4-(3-chlorophenyl)-1-ethyl-7-formyl-2-oxo-1,2-dihydro-1,8-naphthyridin-3-yl]propanoate

Product 1

HCID 1363883733-[4-(3-Chlorophenyl)-1-ethyl-7-hydroxyiminomethyl-2-oxo-1,2-dihydro-1,8-naphthyridin-3-yl]propanoic acidYield 4.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a 33 ml methanol-pyridine (10:1) solution containing 1.50 g of methyl 3-[4-(3-chlorophenyl)-1-ethyl-7-formyl-2-oxo-1,2-dihydro-1,8-naphthyridin-3-yl]propanoate was added 300 mg of hydroxylamine hydrochloride under ice cooling. After stirring for 1 hour, the reaction mixture was diluted with water and extracted with ethyl acetate. The organic layer was washed with water and saturated brine and then the solvent was evaporated. The resulting residue was treated in a similar manner to Example 2 to obtain 72 mg of 3-[4-(3-chlorophenyl)-1-ethyl-7-hydroxyiminomethyl-2-oxo-1,2-dihydro-1,8-naphthyridin-3-yl]propanoic acid as colorless crystals.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water and saturated brine
  3. customthe solvent was evaporated
  4. additionThe resulting residue was treated in a similar manner to Example 2

Sources & evidence

ORD record
ord-dc28954378db4d30931e64f8d23da795
Source dataset
uspto-grants-2004_05
Patent number
US06740662B1

Reaction notes

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