Hydroxyamine hydrochloride → HCID 75182053, compound

HRID 1189053Notes

Reaction equation

HRID 1189053 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([C:8]#[C:9][C:10]2[CH2:15][CH2:14][CH2:13][C:12](=O)[CH:11]=2)[CH:5]=[CH:4][CH:3]=1.Cl.[NH2:18][OH:19]>N1C=CC=CC=1>[CH3:1][C:2]1[N:7]=[C:6]([C:8]#[C:9][C:10]2[CH2:15][CH2:14][CH2:13][C:12](=[N:18][OH:19])[CH:11]=2)[CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 689367313-[(6-Methylpyridin-2-yl)ethynyl]cyclohex-2-en-1-one

Product 1

HCID 75182053HCID 75182053, compoundYield 42.4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 3-(6-methyl-pyridin-2-ylethynyl)-cyclohex-2-enone (422 mg, 2 mmol) and hydroxylamine hydrochloride (278 mg, 4 mmol) in pyridine (20 ml) is stirred for 17 h at RT. After that time the solvent is evaporated in vacuo. The residue is dissolved in ethyl acetate (300 ml) and washed with sat NaHCO3 (1×50 ml). The water phase is extracted with ethyl acetate (1×50 ml). The combined organic phases are dried over Na2SO4, filtered and concentrated in vacuo. The residue (0.45 g) is purified on column chromatography (Silica gel, eluent hexane/ethyl acetate 2:1 v/v) and the fractions containing the desired compound are collected and concentrated in vacuo to yield 0.192 g (yield=42%) of the title compound as light yellow crystals, m.p. 166-168° C.

Workup

  1. customAfter that time the solvent is evaporated in vacuo
  2. dissolutionThe residue is dissolved in ethyl acetate (300 ml)
  3. washwashed
  4. extractionThe water phase is extracted with ethyl acetate (1×50 ml)
  5. dry with materialThe combined organic phases are dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue (0.45 g) is purified on column chromatography (Silica gel, eluent hexane/ethyl acetate 2:1 v/v)
  9. additionthe fractions containing the desired compound
  10. customare collected
  11. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1e74ce7b79e341b896c5db298ac0559d
Source dataset
uspto-grants-2014_03
Patent number
US08674110B2

Reaction notes

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