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Water → 4-(4-Chlorophenyl)-1,2-dimethyl-6-oxo-1,4,5,6-tetrahydro-3-pyridinecarboxylic acid

HRID 734723
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HRID 734723 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:13][C:12](=[O:14])[N:11]([CH3:15])[C:10]([CH3:16])=[C:9]2[C:17]([O:19]C)=[O:18])=[CH:4][CH:3]=1.[OH-].[Na+].O.CCOC(C)=O>CO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]2[CH2:13][C:12](=[O:14])[N:11]([CH3:15])[C:10]([CH3:16])=[C:9]2[C:17]([OH:19])=[O:18])=[CH:6][CH:7]=1
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참가 물질

6

반응물 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 5306292HCID 5306292, 화합물

생성물 1

HCID 688301204-(4-Chlorophenyl)-1,2-dimethyl-6-oxo-1,4,5,6-tetrahydro-3-pyridinecarboxylic acid수율 75%

시약·촉매·용매 1

HCID 887Methanol
용매

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온도
60 °C

실험 절차

The product from step 1 (470 mg, 1.6 mmol, 1.0 equiv) was dissolved in MeOH (10 mL) and 2.5 M NaOH (2.5 mL) was added. The mixture was heated to 60° C. for three hours. When the reaction had cooled to room temperature, water and EtOAc were added. The phases were separated, and the aqueous layer was adjusted to pH 7 with 6N HCl. The aqueous phase was extracted with ethyl acetate. The organic extracts were dried over Na2SO4 and concentrated to dryness. The residue was azeotroped with hexanes to provide 335 mg (75%) of the title compound as a foamy white solid. MS (ES+) m/e 280 [M+H]+.

후처리

  1. temperatureWhen the reaction had cooled to room temperature
  2. customThe phases were separated
  3. extractionThe aqueous phase was extracted with ethyl acetate
  4. dry with materialThe organic extracts were dried over Na2SO4
  5. concentrationconcentrated to dryness
  6. customThe residue was azeotroped with hexanes

출처 및 근거

ORD 기록
ord-6e99dfa51ec84068b054fe533709d1a1
출처 데이터셋
uspto-grants-2009_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07592357B2

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