Hydroxyamine hydrochloride → 4-(3-chlorophenyl)-1-ethyl-7-hydroxyiminomethylpyrido[2,3-d]pyrimidin-2(1H)-one

HRID 368992Notes

Reaction equation

HRID 368992 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[C:9]3[CH:20]=[CH:19][C:18]([CH:21]=O)=[N:17][C:10]=3[N:11]([CH2:15][CH3:16])[C:12](=[O:14])[N:13]=2)[CH:5]=[CH:6][CH:7]=1.Cl.[NH2:24][OH:25].C([O-])(=O)C.[Na+]>CO>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[C:9]3[CH:20]=[CH:19][C:18]([CH:21]=[N:24][OH:25])=[N:17][C:10]=3[N:11]([CH2:15][CH3:16])[C:12](=[O:14])[N:13]=2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 23284478HCID 23284478, compound

Product 1

HCID 1363337144-(3-chlorophenyl)-1-ethyl-7-hydroxyiminomethylpyrido[2,3-d]pyrimidin-2(1H)-oneYield 18%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4-(3-Chlorophenyl)-1-ethyl-2-oxo-1,2-dihydropyrido[2,3-d]pyrimidine-7-carbaldehyde (900 mg, 2.9 mmol) was dissolved in 10 ml of methanol, 420 mg (6.0 mmol) of hydroxylamine hydrochloride and 550 mg (6.7 mmol) of sodium acetate were added thereto, followed by stirring overnight at room temperature. The insoluble matter was washed with water and chloroform and recrystallized from dimethylformamide-acetonitrile to give 171 mg (18%) of 4-(3-chlorophenyl)-1-ethyl-7-hydroxyiminomethylpyrido[2,3-d]pyrimidin-2(1H)-one.

Workup

  1. washThe insoluble matter was washed with water and chloroform
  2. customrecrystallized from dimethylformamide-acetonitrile

Sources & evidence

ORD record
ord-4b06b3b2b3f447afb91b2642d2b0c61e
Source dataset
uspto-grants-2000_10
Patent number
US06136810

Reaction notes

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