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

HRID 933
Notes
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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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 962
Water
Solvent
2×

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
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05723473

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes