Acetic Anhydride → HCID 58437297, 화합물

HRID 73324노트

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HRID 73324 반응식
[CH2:1]([O:8][C:9]([C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][CH:19]=1)[NH:16][CH:15]=[C:14]2[CH:20]=O)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[NH2:23]O.C(OC(=O)C)(=O)C.[OH-].[Na+]>O1CCCC1.N1C=CC=CC=1>[CH2:1]([O:8][C:9]([C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][CH:19]=1)[NH:16][CH:15]=[C:14]2[C:20]#[N:23])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

7

반응물 4

HCID 7918Acetic AnhydrideHCID 14798Sodium HydroxideHCID 443297Hydroxyamine hydrochlorideHCID 58437409HCID 58437409, 화합물

생성물 1

HCID 58437297HCID 58437297, 화합물수율 65.8%

시약·촉매·용매 2

HCID 1049Pyridine용매HCID 8028Tetrahydrofuran용매

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온도
80 °C

실험 절차

To a solution of 3-formyl-1H-indole-5-carboxylic acid benzyl ester (4.3 g) and pyridine (4.8 g) in tetrahydrofuran (60 ml) was added hydroxylamine hydrochloride (1.6 g) at room temperature and this mixture was stirred at 80° C. overnight. Acetic anhydride was added to reaction mixture at the same temperature and this mixture was stirred for 8 hours. After cooling to ambient temperature, 1 mol/L sodium hydroxide solution (20 mL) was added to this mixture and resulting mixture was extracted with diethyl ether. The organic layer was washed with brine, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure and this residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate) to give the title compound (2.8 g).

후처리

  1. stirringthis mixture was stirred for 8 hours
  2. temperatureAfter cooling to ambient temperature
  3. customresulting mixture
  4. extractionwas extracted with diethyl ether
  5. washThe organic layer was washed with brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customThe solvent was removed under reduced pressure
  8. customthis residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate)

출처 및 근거

ORD 기록
ord-71f4a3ca11e54f5f913e7eb2875c510b
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08829040B2

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