Hydrochloric Acid → 1-(1H-pyrrolo[2,3-c]pyridin-2-yl)ethanone oxime

HRID 1821869Notes

Reaction equation

HRID 1821869 reaction equation
[NH:1]1[C:5]2=[CH:6][N:7]=[CH:8][CH:9]=[C:4]2[CH:3]=[C:2]1[C:10](=O)[CH3:11].[NH2:13][OH:14].Cl.[Li+].[OH-]>C(O)C.O>[NH:1]1[C:5]2=[CH:6][N:7]=[CH:8][CH:9]=[C:4]2[CH:3]=[C:2]1[C:10](=[N:13][OH:14])[CH3:11]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 787HydroxylamineHCID 3939Lithium HydroxideHCID 552679001-(1H-pyrrolo[2,3-c]pyridin-2-yl)ethanone

Product 1

HCID 1363865051-(1H-pyrrolo[2,3-c]pyridin-2-yl)ethanone oximeYield 47%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of 1-(1H-pyrrolo[2,3-c]pyridin-2-yl)ethanone (Example 70) (0.39 g, 2.42 mmol) and hydroxylamine.HCl (0.34 g, 4.84 mmol) in ethanol (12.1 mL) and water (3.4 mL) was added LiOH (0.31 g, 7.26 mmol). The reaction mixture was refluxed for 1.0 h, and then the heat was removed. After concentration under reduced pressure, the residue was triturated with water. The solid was collected by filtration, rinsed with water and Et2O, and dried under vacuum at 45° C. to give 1-(1H-pyrrolo[2,3-c]pyridin-2-yl)ethanone oxime (0.20 g, 47%) as a yellow solid: 1H NMR (300 MHz, CD3OD) δ2.26 (3H, s), 6.78 (1H, s), 7.54-7.57 (1H, m), 8.03 (1H, d, J=5.6 Hz), 8.64 (1H, s); ESI MS m/z 176 [C9H9N3O+H]+; HPLC (Method A) >99% (AUC, isomeric ratio=89.3:10.7), tR=12.47 (major) and 12.25 (minor).

Workup

  1. temperatureThe reaction mixture was refluxed for 1.0 h
  2. customthe heat was removed
  3. concentrationAfter concentration under reduced pressure
  4. customthe residue was triturated with water
  5. filtrationThe solid was collected by filtration
  6. washrinsed with water and Et2O
  7. customdried under vacuum at 45° C.

Sources & evidence

ORD record
ord-a0639070bfca499d8f5160fc4a0b6767
Source dataset
uspto-grants-2009_10
Patent number
US07608627B2

Reaction notes

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