Hydrochloric Acid → 7-Bromo-8-hydroxymethyl-3,3-dimethyl-3,4-dihydro-1H-quinoxalin-2-one

HRID 871967노트

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HRID 871967 반응식
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Br:7][C:8]1[C:17]([C:18](OC)=[O:19])=[C:16]2[C:11]([NH:12][C:13]([CH3:24])([CH3:23])[C:14](=[O:22])[NH:15]2)=[CH:10][CH:9]=1.C(OCC)(=O)C.Cl>O1CCCC1.O>[Br:7][C:8]1[C:17]([CH2:18][OH:19])=[C:16]2[C:11]([NH:12][C:13]([CH3:24])([CH3:23])[C:14](=[O:22])[NH:15]2)=[CH:10][CH:9]=1

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 21226445Aluminium lithium hydrideHCID 24780709Methyl 6-bromo-2,2-dimethyl-3-oxo-1,2,3,4-tetrahydroquinoxaline-5-carboxylate

생성물 1

HCID 576720007-Bromo-8-hydroxymethyl-3,3-dimethyl-3,4-dihydro-1H-quinoxalin-2-one수율 74%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매2회

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온도
0 °C

실험 절차

Lithium aluminium hydride (38.5 mg, 1.01 mmol) was suspended in anhydrous tetrahydrofuran (0.5 mL) under nitrogen atmosphere. An anhydrous tetrahydrofuran solution (1.5 mL) of 7-bromo-8-methoxycarbonyl-3,3-dimethyl-3,4-dihydro-1H-quinoxalin-2-one (Reference Compound No. 1, 101 mg, 0.323 mmol) was added dropwise thereto at 0° C., and stirred for 1 hour at the same temperature. Ethyl acetate (10 mL), water (10 mL), and 1N aqueous hydrochloride solution (2 mL) were added thereto successively and the mixture was partitioned. The organic layer was washed with saturated brine (10 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 (67.4 mg) as an orange amorphous product. (Yield 74%)

후처리

  1. customsuccessively and the mixture was partitioned
  2. washThe organic layer was washed with saturated brine (10 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-c5e9a23231bc449bb1e3207edcfe835f
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08975256B2

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