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Water → 7-(5-Chloro-2-hydroxyphenyl)-8-hydroxymethyl-1,3,3-trimethyl-3,4-dihydro-1H-quinoxalin-2-one

HRID 871974
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인쇄 미리보기

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HRID 871974 반응식
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl:7][C:8]1[CH:25]=[C:24]2[C:11]([O:12][C:13](=[O:30])[C:14]3[C:23]2=[CH:22][CH:21]=[C:20]2[C:15]=3[N:16]([CH3:29])[C:17](=[O:28])[C:18]([CH3:27])([CH3:26])[NH:19]2)=[CH:10][CH:9]=1.C(OCC)(=O)C.O>O1CCCC1.[Cl-].[Na+].O>[Cl:7][C:8]1[CH:9]=[CH:10][C:11]([OH:12])=[C:24]([C:23]2[C:14]([CH2:13][OH:30])=[C:15]3[C:20]([NH:19][C:18]([CH3:26])([CH3:27])[C:17](=[O:28])[N:16]3[CH3:29])=[CH:21][CH:22]=2)[CH:25]=1
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참가 물질

7

반응물 4

HCID 962WaterHCID 8857Ethyl Acetate2회HCID 21226445Aluminium lithium hydrideHCID 576717409-Chloro-2,2,4-trimethyl-1,4-dihydro-2H-6-oxa-1,4-diazachrysen-3,5-dione

생성물 1

HCID 247808507-(5-Chloro-2-hydroxyphenyl)-8-hydroxymethyl-1,3,3-trimethyl-3,4-dihydro-1H-quinoxalin-2-one수율 69%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매2회
HCID 57417360Sodium chloride; water용매

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온도
-10 °C

실험 절차

Lithium aluminium hydride (442 mg, 11.7 mmol) was suspended in anhydrous tetrahydrofuran (10 mL) under nitrogen atmosphere. An anhydrous tetrahydrofuran solution (40 mL) of 9-chloro-2,2,4-trimethyl-1,4-dihydro-2H-6-oxa-1,4-diazachrysen-3,5-dione (Reference Compound No. 11-1, 1:99 g, 5.81 mmol) was added dropwise thereto at −10° C. and stirred for 10 minutes at the same temperature. After ethyl acetate (1 mL) and water (1 mL) were added thereto successively, ethyl acetate (300 mL) and saturated brine (300 mL) were added and partitioned. The organic layer was washed with saturated brine (150 mL), dried over anhydrous magnesium sulfate, and then the solvent was removed under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate) to give the titled reference compound (1.38 g) as a pale yellow solid. (Yield 69%)

후처리

  1. custompartitioned
  2. washThe organic layer was washed with saturated brine (150 mL)
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was removed under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate)

출처 및 근거

ORD 기록
ord-b3d06372cfef4a94acaf71fc7e9678df
출처 데이터셋
uspto-grants-2015_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08975256B2

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