Diisopropylethylamine → HCID 72628750, compound

HRID 1964794Notes

Reaction equation

HRID 1964794 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=O)=[CH:4][CH:3]=1.CCN(C(C)C)C(C)C.Cl.[NH2:26][OH:27]>CCO>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[N:26][OH:27])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 443297Hydroxyamine hydrochlorideHCID 3061713Methanone, (6-chloro-3-pyridinyl)phenyl-

Product 1

HCID 72628750HCID 72628750, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The ketone issued from the precedent step (XIX*), e.g., (6-chloropyridin-3-yl)(phenyl)methanone (435 mg, 2 mmol), was dissolved in EtOH (40 mL). DIEA (1.027 mL, 6 mmol) and hydroxylamine hydrochloride (417 mg; 6 mmol) were added. The mixture was heated under reflux overnight. The solvents were removed. The resulting crude mixture was dissolved in ethyl acetate (40 mL) and was washed with three portions of water. The organic layer was dried over magnesium sulfate, filtrated and evaporated to give the desired product (XXXXIII*), e.g., (6-chloropyridin-3-yl)(phenyl)methanone oxime (413 mg, 89% yield). It was used in the next step without further purification.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux overnight
  3. customThe solvents were removed
  4. dissolutionThe resulting crude mixture was dissolved in ethyl acetate (40 mL)
  5. washwas washed with three portions of water
  6. dry with materialThe organic layer was dried over magnesium sulfate
  7. filtrationfiltrated
  8. customevaporated

Sources & evidence

ORD record
ord-2edc374d2deb44d1b20dfc9f3753b0fa
Source dataset
uspto-grants-2013_04
Patent number
US08415480B2

Reaction notes

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