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Potassium Hydroxide → HCID 22048327, 화합물

HRID 1833169
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HRID 1833169 반응식
C(OC([N:6]1[CH:15]=[C:14]([CH:16]=[O:17])[C:13]2[C:8](=[CH:9][C:10]([O:26][CH3:27])=[C:11]([O:18][CH2:19][CH2:20][CH2:21][O:22][C:23](=[O:25])[CH3:24])[CH:12]=2)[CH:7]1[CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[C:31]([O:35][CH3:36])[CH:30]=1)=O)C.[OH-].[K+]>CO>[C:23]([O:22][CH2:21][CH2:20][CH2:19][O:18][C:11]1[CH:12]=[C:13]2[C:8](=[CH:9][C:10]=1[O:26][CH3:27])[CH:7]([CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[C:31]([O:35][CH3:36])[CH:30]=1)[NH:6][CH:15]=[C:14]2[CH:16]=[O:17])(=[O:25])[CH3:24]
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참가 물질

4

반응물 2

HCID 14797Potassium HydroxideHCID 86595639HCID 86595639, 화합물

생성물 1

HCID 22048327HCID 22048327, 화합물수율 67%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

To a stirred solution of 6-(3-acetoxy-propoxy)-4-formyl-7-methoxy-1-(3-methoxy-benzyl)-1H-isoquinoline-2-carboxylic acid ethyl ester (150 mg, 0.30 mmol) in methanol (6 mL) was added powdered potassium hydroxide (169 mg, 3.0 mmol). The reaction mixture was stirred at room temperature for 3 hrs. The solvent was evaporated and the residue was diluted with ethyl acetate (20 mL) and water (20 mL). The aqueous phase was extracted with ethyl acetate (3×20 mL). The combined extracts were washed with saturated aqueous sodium chloride solution (20 mL), dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo to afford 6-(3-acetoxy-propoxy)-7-methoxy-1-(3-methoxy-benzyl)-1,2-dihydro-isoquinoline-4-carbaldehyde (78 mg, 67% yield) as a yellow oil. The crude product was used without further purification. To a stirred solution of 6-(3-acetoxy-propoxy)-7-methoxy-1-(3-methoxy-benzyl)-1,2-dihydro-isoquinoline-4-carbaldehyde (78 mg, 0.20 mmol) in chloroform (3 mL) was added manganese (IV) oxide (208 mg, 2.0 mmol). The reaction mixture was stirred at room temperature for 15 hrs, filtered through a Celite® pad, and washed with chloroform. The filtrate was concentrated in vacuo to afford 6-(3-acetoxy-propoxy)-7-methoxy-1-(3-methoxy-benzyl)-isoquinoline-4-carbaldehyde (20 mg, 23% yield). The crude product was used without further purification.

후처리

  1. customThe solvent was evaporated
  2. additionthe residue was diluted with ethyl acetate (20 mL) and water (20 mL)
  3. extractionThe aqueous phase was extracted with ethyl acetate (3×20 mL)
  4. washThe combined extracts were washed with saturated aqueous sodium chloride solution (20 mL)
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-caad4f02840541fc9b80eb2ea291269c
출처 데이터셋
uspto-grants-2006_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07067529B2

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