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Potassium Carbonate → 1-Bromo-4-hydroxy-7-phenylsulfanyl-isoquinoline-3-carboxylic acid methyl ester

HRID 523844
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반응식

HRID 523844 반응식
[Br:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([S:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH:10]=2)[C:5]([OH:19])=[C:4]([C:20]([OH:22])=[O:21])[N:3]=1.[C:23](=O)([O-])[O-].[K+].[K+].S([O-])(OC)(=O)=O>CC(C)=O>[CH3:23][O:21][C:20]([C:4]1[N:3]=[C:2]([Br:1])[C:11]2[C:6]([C:5]=1[OH:19])=[CH:7][CH:8]=[C:9]([S:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH:10]=2)=[O:22]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 4694097Methyl sulfate(1-)HCID 860145681-Bromo-4-hydroxy-7-phenylsulfanyl-isoquinoline-3-carboxylic acid

생성물 1

HCID 865954711-Bromo-4-hydroxy-7-phenylsulfanyl-isoquinoline-3-carboxylic acid methyl ester수율 92.5%

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

1-Bromo-4-hydroxy-7-phenylsulfanyl-isoquinoline-3-carboxylic acid (10.0 g), potassium carbonate (3.7 g) and methyl sulfate (3.4 g) were suspended in 500 ml acetone and stirred at reflux overnight. Reaction mixture was concentrated and residue partitioned between 1N hydrochloric acid and ethyl acetate. Organic layer was dried over magnesium sulfate and filtered. Filtrate concentrated to give title compound (9.6 g). MS-(+)-ion M+1=389.9, 391.9.

후처리

  1. temperatureat reflux overnight
  2. customReaction mixture
  3. concentrationwas concentrated
  4. customresidue partitioned between 1N hydrochloric acid and ethyl acetate
  5. dry with materialOrganic layer was dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationFiltrate concentrated

출처 및 근거

ORD 기록
ord-71911245d3744795af9df003b3716c18
출처 데이터셋
uspto-grants-2016_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09339527B2

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