O-ethylhydroxylamine hydrochloride → HCID 136153566, compound

HRID 542665Notes

Reaction equation

HRID 542665 reaction equation
[OH:1][C:2]1[CH2:7][CH:6]([C:8]2[C:9]([CH3:16])=[N:10][C:11]([CH3:15])=[N:12][C:13]=2[CH3:14])[CH2:5][C:4](=[O:17])[C:3]=1[C:18](=O)[CH2:19][CH2:20][CH3:21].Cl.[CH2:24]([O:26][NH2:27])[CH3:25].O.O.O.C([O-])(=O)C.[Na+]>C(O)C>[CH2:24]([O:26][N:27]=[C:18]([C:3]1[C:4](=[O:17])[CH2:5][CH:6]([C:8]2[C:9]([CH3:16])=[N:10][C:11]([CH3:15])=[N:12][C:13]=2[CH3:14])[CH2:7][C:2]=1[OH:1])[CH2:19][CH2:20][CH3:21])[CH3:25]

Participants

5

Reactant 3

HCID 76850O-ethylhydroxylamine hydrochlorideHCID 23665404Sodium Acetate TrihydrateHCID 178450337HCID 178450337, compound

Product 1

HCID 136153566HCID 136153566, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3-Hydroxy-5-(2,4,6-trimethylpyrimidin-5-yl)-2-butyrylcyclohex-2-en-1-one (0.29 g) was stirred with O-ethylhydroxylamine hydrochloride (0.1 g) and sodium acetate trihydrate (0.14 g) in ethanol (30 ml) at room temperature for 15 hr. The mixture was poured into a saturated aqueous salt solution (50 ml), which was subsequently extracted with ethyl acetate. The dried (Na2SO4) organic extract was evaporated to give 2-[1-(ethoxyimino)butyl]-3-hydroxy-5-(2,4,6-trimethylpyrimidin-5-yl)cyclohex-2-en-1-one as a colourless oil. Pmr spectrum (CDCl3 ; δ in ppm): 1.01 (3H, t); 1.34 (3H, t); ca 1.64 (2H, m); ca 2.3-3.8 (7H, m); 2.59 (6H, s); 2.63 (3H, s); 4.13 (2H, q); 10.66 (1H,s).

Workup

  1. extractionwas subsequently extracted with ethyl acetate
  2. dry with materialThe dried (Na2SO4)
  3. extractionorganic extract
  4. customwas evaporated

Sources & evidence

ORD record
ord-f225b8e2da2b423b8f91a83b94f4e25e
Source dataset
uspto-grants-1987_04
Patent number
US04659362

Reaction notes

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