Hydroxylamine → 2-Acetyl-4-(pyrid-2-yl)-pyrimidine oxime

HRID 933

Reaction equation

HRID 933 reaction equation
[C:1]([C:4]1[N:9]=[C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=2)[CH:7]=[CH:6][N:5]=1)(=O)[CH3:2].[NH2:16][OH:17].C([O-])(=O)C.[Na+]>C(O)C.O>[C:1](=[N:16][OH:17])([C:4]1[N:9]=[C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=2)[CH:7]=[CH:6][N:5]=1)[CH3:2]

Participants

6

Reactant 3

HCID 787HydroxylamineHCID 517045Sodium AcetateHCID 196942132-Acetyl-4-(pyrid-2-yl)-pyrimidine

Product 1

HCID 1363959922-Acetyl-4-(pyrid-2-yl)-pyrimidine oximeYield 91.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

A solution of 2-acetyl-4-(pyrid-2-yl)-pyrimidine (1.0 g), hydroxylamine (0.39 g) and sodium acetate (0.62 g) in a mixture of ethanol (10 ml) and water (2 ml) was heated to reflux for 1.5 hours. The reaction was then poured into water the precipitate filtered and washed with hexane to give 2-acetyl-4-(pyrid-2-yl)-pyrimidine oxime (0.98 g, 91% yield) as a white crystalline solid m.p. 196°-8° C.; 1H NMR: 2.50(3H,s); 7.42(1H,m); 7.88(1H,m); 8.30(1H,d); 8.59(1H,d); 8.74(1H,d); 8.90(1H,d); 10.85(1H,brs) ppm.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 1.5 hours
  3. filtrationfiltered
  4. washwashed with hexane

Sources & evidence

ORD record
ord-25314cafe14044c4a971af24b93211f4
Source dataset
uspto-grants-1998_03
Patent number
US05723473

Linked notes

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