Water → HCID 136386495, compound

HRID 1821844Notes

Reaction equation

HRID 1821844 reaction equation
[C:1]1([C:7]([C:9]2[NH:17][C:12]3=[CH:13][N:14]=[CH:15][CH:16]=[C:11]3[CH:10]=2)=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.[NH2:19][OH:20].O[Li].O.O>C(O)C>[C:1]1([C:7]([C:9]2[NH:17][C:12]3=[CH:13][N:14]=[CH:15][CH:16]=[C:11]3[CH:10]=2)=[N:19][OH:20])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 443297Hydroxyamine hydrochlorideHCID 57893467phenyl(1H-pyrrolo[2,3-c]pyridin-2-yl)methanone

Product 1

HCID 136386495HCID 136386495, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a mixture of phenyl(1H-pyrrolo[2,3-c]pyridin-2-yl)methanone (Example 35) (161 mg, 0.72 mmol) and hydroxylamine hydrochloride (100 mg, 1.45 mmol) in ethanol (3.6 mL) were added LiOH.H2O (120 mg, 2.16 mmol) and water (1.0 mL). The reaction mixture was heated under reflux until TLC analysis indicated consumption of the ketone. The mixture was concentrated to dryness. The residue was treated with water, and the residual solid was collected by filtration to give predominately one isomer of phenyl(1H-pyrrolo[2,3-c]pyridin-2-yl)methanone oxime (75.8 mg, 0.31 mmol, 44%) as a yellow solid. The aqueous filtrate was extracted with methylene chloride (3×). The combined extracts were washed with saturated NaCl, dried over Na2SO4, filtered, and concentrated to give ca. 1:1 mixture of isomers of the oxime (72 mg, 0.30 mmol, 42%) as a yellow solid:

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux until TLC analysis
  3. customconsumption of the ketone
  4. concentrationThe mixture was concentrated to dryness
  5. additionThe residue was treated with water
  6. filtrationthe residual solid was collected by filtration

Sources & evidence

ORD record
ord-c7eac558c90842049a2d8e0a1935e01c
Source dataset
uspto-grants-2009_10
Patent number
US07608627B2

Reaction notes

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