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

HRID 871967ノート

反応式

HRID 871967 の反応式
[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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
0 °C

実験手順

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%)

後処理

  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)

出典と根拠

ORDレコード
ord-c5e9a23231bc449bb1e3207edcfe835f
出典データセット
uspto-grants-2015_03
特許番号
US08975256B2

反応ノート

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