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

HRID 1821869노트

반응식

HRID 1821869 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 702Ethanol용매HCID 962Water용매

실험 절차

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).

후처리

  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.

출처 및 근거

ORD 기록
ord-a0639070bfca499d8f5160fc4a0b6767
출처 데이터셋
uspto-grants-2009_10
특허 번호
US07608627B2

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