Hydroxyamine hydrochloride → HCID 20080802, compound

HRID 1653851Notes

Reaction equation

HRID 1653851 reaction equation
[Cl:1][C:2]1[CH:23]=[CH:22][C:5]([O:6][C:7]2[CH:12]=[CH:11][C:10]([C:13]3[C:18](=[O:19])[CH:17]=[C:16]([CH3:20])O[C:14]=3[CH3:21])=[CH:9][CH:8]=2)=[CH:4][CH:3]=1.Cl.[NH2:25][OH:26].C([O-])(=O)C.[Na+]>C(O)C.O>[Cl:1][C:2]1[CH:23]=[CH:22][C:5]([O:6][C:7]2[CH:12]=[CH:11][C:10]([C:13]3[C:18](=[O:19])[CH:17]=[C:16]([CH3:20])[N:25]([OH:26])[C:14]=3[CH3:21])=[CH:9][CH:8]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 20080796HCID 20080796, compound

Product 1

HCID 20080802HCID 20080802, compoundYield 19.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

A mixture of 3-(4-(4-chlorophenoxy)phenyl)-2,6-dimethylpyran-4-one (1.0 g), hydroxylamine hydrochloride (1.06 g), sodium acetate (1.25 g) and water (5 ml) in ethanol (10 ml) was heated at reflux for 3 days. After cooling to rt the mixture was diluted with water (20 ml) and the precipitate filtered off and washed with ethyl acetate. Recrystallisation from DMF afforded the title compound (0.2 g), m.p. 232°-236°, NMR δH (d6-DMSO)7.5-7.4 (2H, d, a 8 Hz), 7.3-7.2 (2H, d, J 8 Hz), 7.15-7.0 (4H, m), 6.75 (1H, s), 2.35 (3H, s), 2.15 (3H, s).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 3 days
  3. filtrationthe precipitate filtered off
  4. washwashed with ethyl acetate
  5. customRecrystallisation from DMF

Sources & evidence

ORD record
ord-616a245e53544fce947af5c0b522ed9c
Source dataset
uspto-grants-1995_04
Patent number
US05403934

Reaction notes

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